The Catalyst-Controlled Divergent Cascade Reactions of Homo-Propargylic Amines and Nitrones: Synthesis of Pyrrolo-Isoxazolidines and γ-Lactams

Article abstract of DOI:10.1002/adsc.201701476

Two controllable one-pot cascade cyclization reactions of homopropargylic amines and nitrones were developed by using different metal Cu and Ag salts. The pyrroloisoxazolidines and γ-lactams were obtained in good to high yields, respectively. Herein, nitr

Full text of DOI:10.1002/adsc.201701476

Title: The catalyst-controlled divergent cascade reactions
of homopropargylic amines and nitrones: Synthesis of
pyrroloisoxazolidines and γ-lactams
Authors: Lingyan Liu, li jing, Weixing Chang, Yuanfang Kong, Yingze
Liu, Boyi Wang, and Shengli Li
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201701476
Link to VoR: http://dx.doi.org/10.1002/adsc.201701476

Advanced Synthesis & Catalysis
10.1002/adsc.201701476
FULL PAPER
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
The catalyst-controlled divergent cascade reactions of homo-
propargylic amines and nitrones: Synthesis of pyrrolo-
isoxazolidines and γ-lactams
a
a
a
a
a
Yuanfang Kong, Yingze Liu, Boyi Wang, Shengli Li, Lingyan Liu,* Weixing
a
a,b
Chang, Jing Li *
a
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin,
00071 (China); phone: +86-22-23501410; email: liulingyan@nankai.edu.cn
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Weijin Road 94#, Nankai District,
Tianjin 300071 (China); phone: +86-13512241731; email: lijing@nankai.edu.cn
3
b
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract. Two controllable one-pot cascade cyclization hydroamination
cyclization-1,3-dipolar
cycloaddition
reactions of homopropargylic amines and nitrones were cascade reaction of homopropargylic amines and nitrones in
developed by using different metal Cu and Ag salts. The the presence of AgOAc.
pyrroloisoxazolidines and γ-lactams were obtained in good
to high yields, respectively. Herein, nitrones played dual Keywords:
Homopropargylic
amines;
Nitrones;
roles, both as 1,3-dipoles and oxidants, and four Hydroamination cyclization cascade reaction; Oxidation;
stereocenters were simultaneously formed in the
1,3-Dipolar cycloaddition
the Lewis acid catalysts may lead to a fatal decrease
of catalytic activity or deoxygenation of nitrones. For
example, Sandhu reported that the nitrones could be
easily transformed to imines by reduction or using
Introduction
The 1,3-dipolar cycloaddition reaction is a very
important reaction in the field of organic synthetic
chemistry. Among them, [3+2]-cycloaddition
reactions of nitrones with olefins are well-developed
various Lewis acid catalysts, such as InCl
3
, Zn(OTf)
2
[5]
and Cu(OTf) .
2
Nevertheless, the studies on the
nitrones as oxidants for providing oxygen sources are
hardly explored besides some studies of pyridine N-
[6]
for the construction of complex molecules,
oxides.
alkaloids.[
1]
The
cycloadducts,
particularly
isoxazolidines, have high synthetic potential based on
their transformations to γ-amino alcohols through
reductive cleavage of the nitrogen-oxygen bond or
[2]
lactam antibiotics through cleavage rearrangement.
Traditionally, 1,3-dipolar cycloadditions are carried
[3a]
out thermally. But since Kanemasa et al. reported
that Lewis acids could accelerate 1,3-dipolar
cycloaddition reaction to achieve both high regio-
and endo/exo-selectivity, many metal-based catalysts,
such as zinc, titanium, and magnesium salts, have
been proposed for 1,3-dipolar cycloaddition reaction
of nitrones.[ Activation modes of the Lewis acid
catalysts are different in the normal- or inverse-
electron demand cycloaddition reactions (Scheme
3]
Scheme 1. The activated modes of 1,3-dipolar
cycloaddition reactions of nitrones.
[4]
1
). In the former, the dipolarophiles are activated by
the Lewis acid catalysts to become more electron-
deficient, thus being easily attacked by the oxygen
anion of the nitrones, but the Lewis acid catalysts
activate the 1,3-dipoles to make the iminium ions
more electron-deficient, and the electron-rich olefins
dipolarophiles attack the activated nitrones in the
latter. Notably, the coordination of nitrones with
On the other hand, the hydroamination cyclization
of homopropargylic amines are generally performed
in the presence of the metal salts (Cu, Ag, Au, Pt,
etc.) or strong bases, and afford dihydropyrrole
intermediates, which may act as dipolarophiles. Our
group had developed a series of hydroamination
cyclization [2+4]- or [4+2]-cycloaddition cascade
reactions of homopropargylic amines for the
1
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Advanced Synthesis & Catalysis
10.1002/adsc.201701476
synthesis of diverse 5-6-6 or 5-6-5 fused N-
containing heterocycles.[ As a continuation of our
ongoing work, we planned to employ nitrones as 1,3-
dipoles to perform the hydroamination cyclization-
catalyst, although only low yield of 3a (36%) was
obtained with most of 1a being decomposed, no other
side products (4a-7a) were observed (entry 5). This
result led us to further fine-tune the other various
7]
[
2+3]-cycloaddition via an inverse-electron demand
Lewis bases in the presence of AgOAc. Consequently,
.
mode with homopropargylic amines for the
construction of fused pyrroloisoxazolidines, which
are ubiquitous in biologically and pharmaceutically
interesting molecules.[ Unexpectedly, two different
products, the pyrroloisoxazolidines 3 and γ-lactams 4,
were controllably obtained through using different
the DABCO 6H
2
O provided the best yield of 75%
o
using 3.0 equiv. nitrone 2a at 80 C (entries 6-16).
Additionally, we attempted to carry out this reaction
in the absence of PhCHO, it was unexpectedly
observed that nearly the same yield of 3a could be
generated (Entry 17). Therefore, the optimal reaction
8]
metal catalysts Cu(OAc)
2
and AgOAc, respectively
conditions were confined as follows: 10 mol%
.
(
Scheme 2). Obviously, herein the nitrones played
AgOAc, 1.2 equiv. DABCO 6H
2
O, 3.0 equiv. nitrone,
o
dual roles, both as 1,3-dipoles and oxidants for
providing oxygen source.
at 80 C under N atmosphere. To the best of our
2
knowledge, this reaction was the first report about the
catalytic without a stoichiometric amount of Ag salts
applied in the hydroamination cyclization of alkynes.
It should be noted that part of the starting material 1a
suffered decomposition in all cases of other Lewis
bases except for the production of 3a in low yields
(
entries 6-14). Moreover, the diastereoselectivities
ratios of the products in all cases were nearly 1:1
1
based on the H NMR of crude products. The
absolute
configuration
of
endo-3a
was
unambiguously confirmed by an X-ray single-crystal
[9]
diffraction (Figure 1).
Table 1. The screening on the reaction conditions of
homopropargylic amine 1a and nitrone 2a for the synthesis
Scheme 2. The catalysts-controlled divergent cascade
reactions of homopropargylic amines 1 and nitrones 2.
a)
of pyrroloisoxazolidines
Results and Discussion
In our initial study, we selected the homo-
propargylic amine 1a and nitrone 2a as model
substrates. However, it was frustrating that the
diverse possible products (3a-7a) were generated at
the same time in the presence of Cu(OTf) no matter
2
Entry Catalyst
Lewis Base
3a Yield (%)b)
how we changed the experimental parameters, which
included the temperature, solvents, additives and the
reaction system concentration as well as the amount
1
2
3
4
5
6
7
8
9
AgSbF
Ag
AgI
6
Et
Et
Et
Et
Et
3
3
3
3
3
N
N
N
N
N
N.R.
N.R.
N.R.
8
36
38
31
22
22
21
2
O
of the Cu(OTf)
2
and additives (Table S1). For
example, as the desired product 3a was delivered in
AgOTf
AgOAc
AgOAc
AgOAc
AgOAc
AgOAc
AgOAc
AgOAc
AgOAc
AgOAc
low or moderate yield through the hydroamination
cyclization-1,3-dipolar
cycloaddition
cascade
2,6-Lutidine
i
reaction, the homopropargylic amine 1a might
perform the formal dimerization to give the 5a.
Additionally, due to the fact that nitrone 2a easily
Pr
2
NEt
DMAP
NMM
DBU
[5]
deoxygenated in the presence of Cu(OTf)
generated imine might also react
2
,
the
with
1
0
1
2
3
4
1
1
1
1
TMEDA
21
64
45
67
i
homopropargylic amine 1a to render 6a and 7a.
Simultaneously, the lactam 4a might also be obtained
due to the oxidability of nitrone.
Considering that, we selected another relatively
weak Lewis acidic Ag salt to catalyze the reaction
between homopropargylic amine 1a and nitrone 2a
Pr
2
NH
DABCO
AgOAc DABCO.6H
AgOAc DABCO.6H
AgOAc DABCO.6H
2
2
O
O
c)
1
6
5
75
d)
e)
1
2
O
76,75
7f) AgOAc DABCO.6H
76
e)
1
2
O
(
Table 1). As a result, these three salts, such as
a)
Reaction conditions: under an
homopropargylic amine 1a (33.1 mg, 0.15 mmol), nitrone
a (44.4 mg, 0.225 mmol, 1.5 equiv.), Lewis base (1.2
equiv.), PhCHO (8 mg, 0.075 mmol, 0.5 equiv.), catalyst
N
2
atmosphere,
AgSbF , Ag O and AgI displayed no catalytic activity
6
2
(
entries 1-3) with the starting materials remaining
2
untouched (entries 1-3). The AgOTf gave a trace of
the target molecule 3a and a great amount of 1a and
(
10 mol%) and PhMe (2 mL) were sequentially added into
2
a was recovered (entry 4). Employing AgOAc as a
2
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Advanced Synthesis & Catalysis
10.1002/adsc.201701476
a Schlenk tube.The reaction was carried out under the
phenylnitrones, the products were obtained in nearly
given reaction conditions and the products were
1:1 ratio of endo-3/exo-3' configuration.
b)
subsequently detected by TLC.
The yield was
1
determined by H NMR using 1,4-dioxane as an internal
standard. 3.0 equiv. nitrone 2a. 3.0 equiv. nitrone 2a,
Table 2. The scope of homopropargylic amines and
a,b)
c)
d)
nitrones
o
e)
f)
8
0 C. Isolated yield. no PhCHO.
Figure 1. The ORTEP drawing of endo-3a.
The scope of homopropargylic amines and nitrones
were then investigated. As shown in Table 2, all aryl
substituted homopropargylic amines 1 and nitrones 2
(
N-terminal or C-terminal) were competent in our
methodology. And these reactions could afford the
hydroamination cyclization-[2+3]-cycloadducts in
good to high yields for the homopropargylic amines
bearing with cycloalkyl or steric hindrance naphthyl
or heteroaryl whether on the C-terminal (3k-3n) or N-
terminal (3g). Notably, the 3l' contained a small
amount of another diastereoisomer. Unfortunately,
when employing other N-alkyl substituted or
unsubstituted homopropargylic amines or nitrones,
these reactions were sluggish. For example, N-Ts
homopropargylic amine only rendered the
hydroamination cyclization product dihydropyrrole in
4
3
4% yield without further [2+3]-dipolar cycloadduct
o generated. As for the 3p, 3s and 3t, only traces of
target compounds were obtained with a large amount
of the starting materials left remaining. In the cases of
N-H homopropargylic amine and N-alkyl (Me and Bn)
nitrones, the reactions were complicated with slight
spots observed in the thin layer chromatography
(
TLC) plate (3q, 3w and 3x). The homopropargylic
amine bearing 2-OH-aryl group on the C-terminal
was decomposed under the standard reaction
conditions without the target compound 3y generated.
Summarily, it could be found that the nitrones have
some limitations. Only N-phenylnitrones with phenyl
and electron-withdrawing substituted phenyl (o-Br, o-
Cl (3r), m-Br (3u) and p-Br (3V)) on the C-terminal
were applicable for our methodology. And the exo-
configuration 3' products were major in all cases of
the nitrones with o-bromo or o-chlorophenyl
substitutents on the C-terminal, whereas for the
unsubstituted phenyl or other site-substituted
3
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Advanced Synthesis & Catalysis
10.1002/adsc.201701476
1
1
1
1
1
1
2
3
4
5
6
7
Cu(OAc)
2
Et
3
N
N
N
N
N
N
N
N
PhMe
DCE
CH Cl
2 2
THF
DMF
3
CH OH
PhMe
PhMe
PhMe
PhMe
88
40
46
80
72
59
80
84
80
72
Cu(OAc)
Cu(OAc)
Cu(OAc)
Cu(OAc)
Cu(OAc)
Cu(OAc)
Cu(OAc)
2
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
2
2
2
2
2
2
d)
1
1
8
9
e)
f)
a)
Reaction conditions: under an
N
2
atmosphere,
2
0
Cu(OAc)
Cu(OAc)
2
Et
Et
3
N
homopropargylic amines 1 (0.15 mmol), nitrones 2 (0.45
f,g)
.
2
1
2
3
N
mmol, 3.0 equiv.), DABCO 6H
2.5 mg, 0.015 mmol, 0.1 equiv.) and PhMe (2 mL) were
sequentially added into a Schlenk tube. The reaction was
2
O (1.2 equiv.), AgOAc
a)
(
Reaction conditions: to a dried Schlenk tube were added
homopropargylic amine 1a (66.4 mg, 0.3 mmol, 1.5
equiv.), nitrone 2a (0.2 mmol, 1.0 equiv), catalyst (10
mol%), and the reaction vessel was evacuated and
backfilled with nitrogen three times. Then the solvent (2
mL), base (1.2 equiv.), and benzaldehyde (10.6 mg, 0.5
equiv.) were added under a nitrogen atmosphere. The
o
b)
carried out at 80 C and detected by TLC. Isolated yield.
Using 20 mol% AgOAc, 120 C. The product was the
dimerization compound 5r of homopropargylic amine.
c)
o
d)
e)
o
The temperature was 120 C.
o
reaction mixture was stirred at 50 C for about 5 h until
complete disappearance of 2a (monitored by TLC).
b)
In Table S1, the γ-lactam 4a was always generated
as a major side product. We, therefore, anticipated
that a single lactam could be obtained through
controlling reaction conditions. The Lewis bases were
c)
Isolated yield.
2 3
K CO cannot dissolve in the PhMe. But it
d)
can dissolve in the THF and can obtain 25% yield. No
e)
f)
aldehyde. No aldehyde, Cu(OAc)
No aldehyde, Cu(OAc) (1.8 mg, 5 mol%), 1a (0.2 mmol,
.0 equiv.), 2a (0.3 mmol, 1.5 equiv). air.
2
(1.8 mg, 5 mol%).
first examined in the presence of Cu(OTf)
2
. It was
2
g)
found that the Et N gave the best results (Table 3,
3
1
entries 1-5). Subsequently, the Cu(I) and other Cu(II)
salts were carefully screened and high yield of lactam
4
a (88%) could be achieved with the Cu(OAc)
2
Since the nitrone 2a only acted as an oxygen
catalyst (entries 6-12). The solvents were also further
investigated and the PhMe was found to be the
optimal media (entries 13-17). Adjusting other
experimental parameters, such as the 1a/2a ratio, the
source in this reaction, with the removal of imine
which could not further react with the excess
homopropargylic amine 1a (Scheme S1), we
[10]
attempted to apply other oxidants , such as TEMPO,
t
loading of Cu(OAc)
or air (entries 18-21), we observed that using 5
mol% Cu(OAc) and 1.2 equiv. Et N, the reaction of
a and 2a in ratio 1/1.5 also gave a good yield of
2
, with or without aldehyde and
O balloon, BuOOH and 8-methylquinoline 1-oxide
2
N
2
under the standard reaction conditions. Unfortunately,
the results were unsatisfactory (Scheme 3).
Nevertheless, using other similar nitrones 2, the
expected lactams could be obtained in moderate to
good yields (Table S2). The reason remained unclear
at present. Maybe the nitrones possess certain special
oxidability for providing the oxygen.
2
3
1
o
lactam at 50 C under N
of an aldehyde (entry 20).
2
atmosphere in the absence
Table 3. Optimization of reaction conditions of homo-
propargylic amine 1a and nitrone 2a for the synthesis of
lactam)
the
solvent
Entry
Catalyst
Base
Et
Yield (%)b)
1
2
Cu(OTf)
Cu(OTf)
2
3
N
PhMe
PhMe
63
55
Scheme 3. The screening of other oxidants for the
homopropargylic amine 1a.
2
DBU
3
4
Cu(OTf)
2
PhMe
10
Cu(OTf)
Cu(OTf)
2
2
t-BuOK
K CO
2 3
PhMe
PhMe
PhMe
PhMe
PhMe
PhMe
PhMe
PhMe
29
trace
51
65
46
73
70
N.R.
This hydroamination cyclization-oxidation cascade
reaction was further studied by modifying the
homopropargylic amines substrates under the
optimized reaction conditions (Table 3, entry 20). As
shown in Table 4, various aryl substituted
homopropargylic amines whether on the C-terminal
or N-terminal, could all render good yields of target
compounds (4a-4h, 4k-4r). The homopropargylic
c)
5
6
7
8
9
CuCl
CuBr
2
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
N
N
N
N
N
N
2
CuCl
CuBr
CuI
1
1
0
1
Fe(OTf)
3
4
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Advanced Synthesis & Catalysis
10.1002/adsc.201701476
amines bearing steric hindrance naphthyl, heteroaryl,
requisite of the nitrone 2a. Moreover, it could be
found that the nitrone 2a was more easily subjected to
cyclohexyl and cinnamyl substituents on the C-
terminal were also good candidates (4s-4v). However, deoxygenation with Cu(OAc)
2
than AgOAc
according to the eq.3 and eq.4. Additionally, when
adding two catalysts Cu(OAc) and AgOAc together
only traces of lactams were observed in the cases of
t
the N-Ts and N- BuSO homopropargylic amines (4i
2
and 4j).
into the reaction system of 1a and 2a, only the
product 4a was formed within 2 h, but 3a was also
slowly generated with the prolonged reaction time for
Table 4. The scope of homopropargylic amines 1 and
a,b)
nitrone 2a
7
h (eq.5). No reaction occurred in the presence of
Lewis base without any metal catalyst (eq.6).
Moreover, the isolated product 3a could not be
further transformed to 4a under the standard reaction
conditions for the synthesis of γ-lactam (eq.7). From
all of these experiments, we could reveal that the
activity of Cu(OAc) was higher than that of AgOAc
2
in our reactions. On the other hand, because of the
instability and inseparability of N-Ph dihydropyrrole,
we had no choice but to choose the N-Ts dipyrroline
8
as an alternative to react with nitrone 2a in these
two optimal catalytic systems (Scheme 4, eq.8 and
eq.9). Consequently, the starting materials remained
nearly untouched in two cases.
Scheme 4. The controlled experiments
Based on all of the above results and precedents in
a)
[11]
Reaction conditions: Cu(OAc)
2
(5mol%), Et
3
N (1.2
the literature,
two possible cascade reaction
equiv.), 1 (0.2 mmol), and 2a (0.3 mmol, 1.5 equiv.) at 50
mechanisms were proposed for the synthesis of
pyrroloisoxazolidines and lactams, respectively
o
b)
2
C in PhMe (2 mL) under N atmosphere. Isolated yield.
(
Scheme 5). In the presence of AgOAc, the
homopropargylic amine 1a was first activated by the
AgOAc to give intermediate A, attacked by the
oxygen anion of the nitrone 2a, to form B, which
subsequently underwent intramolecular hydro-
amination cyclization and attacked the imine ion to
give the expected cycloadduct 3a with the removal of
In a bid to gain insight into the above two cascade
reaction mechanisms, we performed some additional
control experiments (Scheme 4). In eq.1 and eq.2, the
great amount of homopropargylic amine 1a remained
in the absence of nitrone 2a, with the trace of a
formal dimerization product 5a generated in AgOAc
and a small amount of 1a decomposed in Cu(OAc)
2
.
AgOAc. While in the case of the Cu(OAc) , the
2
The results of these two experiments indicated the
nitrone 2a was coordinated with Cu(OAc) to form
2
5
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Advanced Synthesis & Catalysis
10.1002/adsc.201701476
temperature and was concentrated in vacuo. The crude
high active species C, which was attacked by the
homopropargylic amine 1a to give the alkynyl copper
compound D. This intermediate underwent
intramolecular hydroamination cyclization to afford
the species E, which suffered the cleavage of N-O
bond to render the intermediate F in the presence of
1
product obtained was determined by H NMR to give the
dr value and purified by column chromatography on silica
gel (PE/EtOAc = 150:1) to afford 3.
Synthesis and Characterization of the γ-lactams 4
2
To a dried Schlenk tube were added Cu(OAc) (1.8 mg,
1
HOAc with the removal of imine G traced by the H
5
mol%), nitrone (0.3 mmol, 1.5 equiv), the
homopropargylic amine (0.2 mmol, 1 equiv.) , and the
reaction vessel was evacuated and backfilled with nitrogen
three times. Then the PhMe solvent (2mL) and NEt
NMR of crude product. The intermediate F was
finally transformed to target compound 4a with the
removal of Cu salt.
3
(
1.2eq) were added under a nitrogen atmosphere. The
reaction mixture was stirred at 50 ℃ for about 2 h until
complete disappearance of 1a (monitored by TLC). The
crude product was purified by column chromatography on
silica gel (PE/EtOAc=5:1) to afford 4a as yellow solid,
3
8mg, 80%.
2
-((1-phenylbut-3-yn-1-yl)amino)phenol (1g): yield:
1
3
.286 g (69%); yellow liquid; H NMR (400 MHz,
Chloroform-d) δ 7.27 – 7.22 (m, 2H), 7.22 – 7.15 (m, 2H),
7
6
1
2
.14 – 7.07 (m, 1H), 6.56 (ddd, J = 6.8, 3.9, 2.3 Hz, 2H),
.48 (td, J = 7.5, 1.6 Hz, 1H), 6.34 (dd, J = 8.1, 1.6 Hz,
H), 4.87 (s, 2H), 4.36 (t, J = 6.3 Hz, 1H), 2.66 – 2.49 (m,
13
3
H), 1.93 (t, J = 2.6 Hz, 1H). C NMR (101 MHz, CDCl )
δ 144.6, 142.1, 135.4, 128.7, 127.7, 126.6, 121.5, 119.0,
1
14.9, 114.5, 80.7, 71.5, 57.4, 28.1. HRMS (ESI+)
+
calculated for
38.1230.
16
C H16NO (M+H ) 238.1232; found
Scheme 5. The possible mechanisms for these two
hydroamination cyclization cascade reactions of
homopropargylic amines and nitrones.
2
(
Z)-N-benzylideneaniline oxide (2a): yield: 1.716 g
o 1
(
44%); white solid; mp 111.9-113.5 C; H NMR (400
MHz, Chloroform-d) δ 8.40 (dd, J = 6.8, 3.0 Hz, 2H), 7.92
s, 1H), 7.77 (dd, J = 7.6, 2.2 Hz, 2H), 7.48 (dt, J = 3.8, 1.4
(
Conclusion
13
Hz, 6H). C NMR (101 MHz, CDCl
31.1, 130.8, 130.1, 129.3, 129.2, 128.8, 121.9.
3
) δ 149.2, 134.7,
1
In summary, two novel catalysts-controlled
cascade reactions between homopropargylic amines
and nitrones were developed, namely, in the presence
of AgOAc, the formal hydroamination cyclization-
(Z)-N-(2-bromobenzylidene)aniline oxide (2d): yield:
o
1
1
.928 g (35%); yellow solid; mp 55.8-61.0 C; H NMR
(
400 MHz, Chloroform-d) δ 9.42 (dd, J = 8.0, 1.7 Hz, 1H),
.33 (s, 1H), 7.73 – 7.68 (m, 2H), 7.57 (dd, J = 8.0, 1.2 Hz,
8
13
[
2+3] cycloaddition cascade reaction occurred and
1H), 7.44 – 7.34 (m, 4H), 7.20 (td, J = 7.6, 1.6 Hz, 1H). C
NMR (101 MHz, CDCl ) δ 149.5, 133.2, 133.0, 131.9,
30.3, 129.8, 129.6, 129.3, 127.9, 124.2, 121.9.
gave an access to the fused pyrroloisoxazolidines 3
with most of exo-configurations, whereas with
3
1
Cu(OAc) , the γ-lactams 4 were generated in good
2
(
Z)-N-(2-chlorobenzylidene)aniline oxide (2r): yield:
o 1
yields through the hydroamination cyclization-
oxidation cascade reaction. The AgOAc and
2
.09 g (45%); yellow solid; mp 80.0-83.0 C; H NMR
(400 MHz, Chloroform-d) δ 9.53 (dd, J = 7.7, 2.0 Hz, 1H),
8
2
(
.43 (s, 1H), 7.83 – 7.75 (m, 2H), 7.48 (ddd, J = 11.4, 6.4,
Cu(OAc) displayed different catalytic properties.
2
13
.1 Hz, 4H), 7.39 (ddd, J = 9.6, 7.5, 1.9 Hz, 2H). C NMR
And the nitrones played dual roles in these two
reactions, one as 1,3-dipoles, the other acted as
oxidants for providing the oxygen. Studies of the
additional applications of pyrroloisoxazolidines and
asymmetric transformations of homopropargylic
amines are in progress in our group.
3
101 MHz, CDCl ) δ 149.6, 133.7, 131.6, 130.6, 130.3,
129.6, 129.4, 129.3, 128.4, 127.3, 121.9.
(Z)-N-(2-methylbenzylidene)aniline oxide (2s): yield:
o
1
2
.156 g (51%); yellow solid; mp 84.5-87.0 C; H NMR
(
400 MHz, Chloroform-d) δ 9.27 (dd, J = 5.7, 3.8 Hz, 1H),
7
7
3
1
.95 (s, 1H), 7.67 – 7.60 (m, 2H), 7.41 – 7.31 (m, 3H),
.26 – 7.20 (m, 2H), 7.13 (dd, J = 5.5, 3.5 Hz, 1H), 2.32 (s,
13
3
H). C NMR (101 MHz, CDCl ) δ 149.6, 137.0, 131.9,
30.7, 130.3, 129.9, 129.2, 129.0, 127.9, 126.4, 121.9, 20.0.
Experimental Section
[
7]
(Z)-N-(2-methoxybenzylidene)aniline oxide (2t):
The Synthesis of homopropargylic amines
and
1
[
12]
yield: 2.672g (59%); yellow liquid; H NMR (400 MHz,
nitrones 2 was performed according to the literature
Chloroform-d) δ 9.40 (dd, J = 8.1, 1.6 Hz, 1H), 8.30 (s,
1
H), 7.73 – 7.65 (m, 2H), 7.44 – 7.27 (m, 5H), 6.99 (t, J =
13
Synthesis and Characterization of the pyrrolo-
isoxazolidines 3
7.7 Hz, 1H), 6.82 (d, J = 8.3 Hz, 1H), 3.77 (s, 4H).
C
NMR (101 MHz, CDCl ) δ 157.5, 149.6, 132.2, 129.7,
3
1
29.4, 129.1, 128.7, 121.8, 120.8, 119.8, 109.9, 55.6.
To a dried Schlenk tube were sequentially added
homopropargylic amines 1 (0.15 mmol, 1.0 equiv.),
nitrones 2 (0.45 mmol, 3.0 equiv), AgOAc (2.5 mg, 10
(Z)-N-(3-bromobenzylidene)aniline oxide (2u): yield:
o
1
2.24 g (40%); yellow solid; mp 96.8-99.2 C; H NMR
(400 MHz, Chloroform-d) δ 8.61 (t, J = 1.8 Hz, 1H), 8.19
– 8.06 (m, 1H), 7.81 (s, 1H), 7.70 – 7.63 (m, 2H), 7.49
(ddd, J = 8.0, 2.0, 1.0 Hz, 1H), 7.41 – 7.34 (m, 3H), 7.25 (t,
2
mol%), DABCO.6H O (39.6 mg, 1.2 equiv), the
corresponding aldehyde (0.5 equiv) and PhMe solvent (2
mL) under a nitrogen atmosphere. After the reaction was
finished as indicated by TLC (reaction time for about 10 h), J = 8.0 Hz, 1H). 13C NMR (101 MHz, CDCl ) δ 148.9,
3
the resulting mixture was allowed to cool to room
6
This article is protected by copyright. All rights reserved.

Advanced Synthesis & Catalysis
10.1002/adsc.201701476
1
1
33.8, 133.2, 132.5, 131.4, 130.3, 130.2, 129.3, 127.6,
22.8, 121.7.
1.9H), 2.17 (ddd, J = 11.6, 8.5, 2.5 Hz, 1H), 1.48 (dd, J =
13
11.5, 9.0 Hz, 0.9H). C NMR (101 MHz, CDCl
3
) δ 150.9,
1
1
50.6, 142.9, 142.7, 142.2, 141.0, 137.6, 129.03, 128.98,
28.94, 128.91, 128.86, 128.84, 128.78, 127.73, 127.29,
(
Z)-N-(4-bromobenzylidene)aniline oxide (2v): yield:
o 1
127.2, 127.1, 126.7, 125.63, 125.57, 123.6, 123.5, 122.7,
3
.194 g (58%); white solid; mp 166.5-167.5 C; H NMR
1
6
21.4, 116.8, 116.2, 116.0, 114.6, 94.6, 92.9, 74.5, 70.8,
(
400 MHz, Chloroform-d) δ 8.32 – 8.22 (m, 2H), 7.90 (s,
4.6, 64.2, 54.3, 50.9, 39.8, 36.0. HRMS (ESI+) calculated
1
H), 7.78 – 7.73 (m, 2H), 7.63 – 7.56 (m, 2H), 7.51 – 7.43
+
13
for C29
H
26ClN
2
O (M+H ) 453.1734; found 453.1723.
(
1
m, 3H). C NMR (101 MHz, CDCl
3
) δ 149.1, 133.5,
32.0, 130.4, 130.2, 129.7, 129.3, 124.9, 121.8.
3
-(2-bromophenyl)-2,5,6-triphenylhexahydro-2H-
pyrrolo[3,2-d]isoxazole (3d) [dr = 25:75]: yield: 58 mg
(
Z)-N-(2-bromobenzylidene)methanamine
oxide
o 1
o
1
(77%); yellow solid, mp 149.5-151.7 C; H NMR (400
(
2w): yield: 2.0 g (93%); white solid; mp 76.0-79.3 C; H
MHz, Chloroform-d) δ 7.87 (dd, J = 7.8, 1.7 Hz, 1H), 7.79
NMR (400 MHz, Chloroform-d) δ 9.21 (dd, J = 8.1, 1.8 Hz,
(
dd, J = 7.8, 1.7 Hz, 0.6H), 7.57 (ddd, J = 8.0, 3.8, 1.2 Hz,
1
=
H), 7.77 (s, 1H), 7.54 (dd, J = 8.0, 1.3 Hz, 1H), 7.32 (td, J
13
1.6H), 7.38 – 7.32 (m, 2H), 7.32 – 7.24 (m, 3H), 7.23 –
7.8, 1.3 Hz, 1H), 7.22 – 7.11 (m, 1H), 3.86 (s, 3H).
) δ 133.8, 132.9, 131.5, 129.6,
29.4, 127.8, 123.2, 55.4. HRMS (ESI+) calculated for
C
7
6
.11 (m, 11H), 7.06 – 7.02 (m, 1H), 7.01 – 6.94 (m, 4H),
.94 – 6.90 (m, 2H), 6.86 (dd, J = 7.9, 6.7 Hz, 1H), 6.83 –
NMR (101 MHz, CDCl
3
1
C
+
6.75 (m, 5H), 6.27 (d, J = 5.2 Hz, 0.6H), 6.23 (d, J = 6.0
Hz, 1H), 5.24 (d, J = 7.5 Hz, 0.6H), 5.19 (s, 1H), 5.01 (dd,
J = 8.3, 2.0 Hz, 0.6H), 4.83 (dd, J = 8.3, 2.4 Hz, 1H), 3.92
8 8
H BrNNaO (M+Na ) 235.9687; found 235.9685.
(
Z)-N-(2-bromobenzylidene)-1-phenylmethanamine
(
dtd, J = 10.1, 7.8, 5.2 Hz, 0.6H), 3.39 (td, J = 8.8, 5.8 Hz,
oxide (2x): yield: 1.884 g (65%); white solid; mp 66.3 -
1
1
1
H), 2.60 (dt, J = 12.8, 8.6 Hz, 1H), 2.42 (ddd, J = 12.5,
0.2, 8.2 Hz, 0.6H), 2.25 (ddd, J = 12.8, 8.9, 2.5 Hz, 1H),
o
1
6
=
8.4 C; H NMR (400 MHz, Chloroform-d) δ 9.28 (dd, J
8.0, 1.7 Hz, 1H), 7.90 (s, 1H), 7.58 (dd, J = 8.0, 1.3 Hz,
H), 7.52 – 7.47 (m, 2H), 7.46 – 7.39 (m, 3H), 7.38 – 7.33
13
.47 (ddd, J = 12.5, 8.0, 2.1 Hz, 0.6H). C NMR (101
1
MHz, CDCl
3
) δ 151.11, 151.09, 144.1, 144.0, 142.8, 142.5,
13
(
m, 1H), 7.21 (td, J = 7.7, 1.7 Hz, 1H), 5.09 (s, 2H). C
1
1
1
1
40.2, 137.8, 132.8, 130.0, 129.3, 129.2, 129.12, 129.09,
NMR (101 MHz, CDCl
1
3
) δ 133.1, 132.9, 132.8, 131.5,
29.0, 128.9, 128.8, 128.1, 127.8, 127.11, 127.06, 125.64,
25.57, 122.6 122.2, 122.1, 121.2, 118.7, 118.6, 115.2,
15.1, 114.7, 114.1, 95.0, 93.6, 74.2, 71.0, 64.9, 64.1, 53.7,
29.51, 129.48, 129.4, 129.2, 129.1, 127.7, 123.5, 72.1.
2
,3,5,6-tetraphenylhexahydro-2H-pyrrolo[3,2-d]
48.2, 40.0, 35.5. HRMS (ESI+) calculated for
+
isoxazole (3a) [dr = 50:50]: yield: 47 mg (75%); yellow
C
29
H
26BrN
2
O (M+H ) 497.1229; found 497.1226.
o
1
solid; mp 157.3-158.3 C;
H NMR (400 MHz,
Chloroform-d) δ 7.51 (d, J = 7.6 Hz, 1H), 7.41 (d, J = 7.5
Hz, 3H), 7.38 – 7.31 (m, 3H), 7.31 – 7.26 (m, 3H), 7.23 (d,
J = 6.5 Hz, 2H), 7.21 – 7.10 (m, 6H), 7.10 – 6.90 (m, 8H),
3
-(2-bromophenyl)-2,5-diphenyl-6-(p-tolyl)hexa-
hydro-2H-pyrrolo[3,2-d]isoxazole (3e) [dr = 31:69]:
o
1
yield: 65 mg (84%); yellow solid; mp 170.8-173.5 C; H
6
.89 – 6.73 (m, 5H), 6.29 (d, J = 5.9 Hz, 0.5H), 6.24 (d, J
NMR (400 MHz, Chloroform-d) δ 7.87 (dd, J = 7.8, 1.7 Hz,
=
5.2 Hz, 1H), 5.06 (d, J = 8.0 Hz, 1H), 4.93 (t, J = 6.8 Hz,
1
3
8
6
H), 7.78 (dd, J = 7.8, 1.7 Hz, 0.4H), 7.56 (ddd, J = 8.0,
.9, 1.3 Hz, 1.4H), 7.39 – 7.23 (m, 4H), 7.22 – 7.11 (m,
H), 7.05 – 6.89 (m, 10H), 6.89 – 6.83 (m, 1H), 6.74 –
.66 (m, 3H), 6.25 (d, J = 5.2 Hz, 0.4H), 6.21 (d, J = 6.0
1
3
1
=
.5H), 4.79 (s, 0.5H), 3.62 (dtd, J = 15.3, 7.4, 5.2 Hz, 1H),
.42 (q, J = 8.0 Hz, 0.5H), 2.60 (dq, J = 12.7, 9.8, 9.2 Hz,
.5H), 2.16 (ddd, J = 12.0, 8.5, 2.3 Hz, 0.5H), 1.45 (ddd, J
1
3
3
12.5, 7.7, 1.9 Hz, 1H). C NMR (101 MHz, CDCl ) δ
Hz, 1H), 5.23 (d, J = 7.6 Hz, 0.4H), 5.18 (s, 1H), 4.97 (dd,
J = 8.2, 2.2 Hz, 0.4H), 4.79 (dd, J = 8.3, 2.5 Hz, 1H), 3.90
1
1
1
1
6
51.2, 151.1, 144.2, 144.1, 142.7, 142.6, 141.2, 138.0,
29.12, 129.08, 128.92, 128.88, 128.86, 128.8, 128.73,
27.65, 127.0, 126.71, 125.67, 125.6, 122.3, 121.2, 118.5,
16.1, 115.0, 114.7, 114.6, 94.6, 93.0, 74.5, 71.0, 64.5,
(
(
dtd, J = 9.9, 7.8, 5.1 Hz, 0.4H), 3.46 – 3.29 (m, 1H), 2.58
dt, J = 12.8, 8.6 Hz, 1H), 2.42 – 2.35 (m, 0.4H), 2.23 (d, J
=
5.0 Hz, 5.2H), 1.46 (ddd, J = 12.5, 8.1, 2.3 Hz, 0.4H).
4.1, 54.2, 50.6, 39.8, 35.9. HRMS (ESI+) calculated for
13
3
C NMR (101 MHz, CDCl ) δ 151.2, 151.2, 143.0, 142.7,
+
C
29
H
27
N
2
O (M+H ) 419.2123; found 419.2116.
1
1
41.71, 141.68, 140.3, 137.9, 132.8, 129.9, 129.70, 129.66,
29.3, 129.1, 128.9, 128.9, 128.9, 128.8, 128.0, 127.8,
2
,3-diphenyl-5,6-di-p-tolylhexahydro-2H-pyrrolo
127.6, 127.04, 126.98, 125.7, 125.6, 122.5, 122.2, 122.0,
121.1, 115.1, 115.1, 114.7, 114.1, 95.2, 93.9, 74.3, 71.1,
[
3,2-d]isoxazole (3b) [dr = 50:50]: yield: 51 mg (76%);
o
1
white solid; mp 74.1-77.3 C; H NMR (400 MHz,
64.8, 64.1, 53.7, 48.1, 40.0, 35.6, 20.6. HRMS (ESI+)
+
Chloroform-d) δ 7.55 – 7.51 (m, 2H), 7.45 – 7.27 (m, 10H), calculated for C30
7
(
H
28BrN
2
O (M+H ) 511.1385; found
.24 (d, J = 2.1 Hz, 1H), 7.18 – 7.12 (m, 3H), 7.09 – 6.99
511.1382.
m, 11H), 6.98 – 6.93 (m, 5H), 6.92 – 6.84 (m, 3H), 6.77 –
6
5
.69 (m, 4H), 6.27 (dd, J = 6.1, 2.6 Hz, 1H), 6.22 (dd, J =
.4, 2.2 Hz, 1H), 5.02 (d, J = 8.1 Hz, 1H), 4.95 (d, J = 5.9
3
-(2-bromophenyl)-6-(4-methoxyphenyl)-2,5-diphen-
yl-hexahydro-2H-pyrrolo[3,2-d] isoxazole (3f): yield: 22
Hz, 1H), 4.88 (d, J = 8.0 Hz, 1H), 4.81 (s, 1H), 3.61 (ddt, J
o
1
mg (28%); yellow solid; mp 166.5-170.8 C; H NMR (400
=
(
10.9, 8.1, 5.8 Hz, 1H), 3.42 (q, J = 8.1 Hz, 1H), 2.57
MHz, Chloroform-d) δ 7.78 (dd, J = 7.8, 1.7 Hz, 1H), 7.57
dddd, J = 21.8, 14.0, 9.9, 2.0 Hz, 2H), 2.29 (dd, J = 6.4,
(
dd, J = 8.0, 1.3 Hz, 1H), 7.34 (td, J = 7.6, 1.3 Hz, 1H),
2
1
1
1
1
1
6
.2 Hz, 6H), 2.25 (t, J = 3.1 Hz, 6H), 2.18 – 2.09 (m, 1H),
13
7
1
3
.30 – 7.26 (m, 2H), 7.25 – 7.22 (m, 2H), 7.18 (td, J = 7.5,
.7 Hz, 2H), 7.05 (dd, J = 7.0, 1.8 Hz, 2H), 7.01 – 6.93 (m,
H), 6.83 – 6.71 (m, 4H), 6.24 (d, J = 5.2 Hz, 1H), 5.22 (d,
3
.46 – 1.37 (m, 1H). C NMR (101 MHz, CDCl ) δ 151.4,
51.2, 142.0, 141.8, 141.3, 139.9, 139.8, 138.2, 136.60,
36.58, 129.7, 129.63, 129.57, 129.5, 128.9, 128.8, 128.7,
27.6, 127.5, 127.1, 126.7, 125.64, 125.57, 122.17, 121.16,
16.0, 115.00, 114.98, 114.6, 94.9, 93.3, 74.6, 71.0, 64.3,
J = 7.6 Hz, 1H), 4.94 (dd, J = 8.1, 2.9 Hz, 1H), 3.97 – 3.86
(
(
m, 1H), 3.73 (s, 3H), 2.34 (dt, J = 12.5, 8.6 Hz, 1H), 1.49
13
ddd, J = 12.4, 8.2, 2.9 Hz, 1H). C NMR (101 MHz,
3.9, 54.2, 50.6, 39.9, 36.1, 21.2, 20.6. HRMS (ESI+)
CDCl
3
) δ 152.8, 151.0, 142.8, 138.2, 137.9, 132.8, 130.0,
+
calculated for
47.2437.
C
31
H
31
N
2
O
(M+H ) 447.2436; found
1
1
29.3, 129.1, 128.9, 127.8, 127.1, 125.8, 122.2, 122.1,
4
16.1, 115.3, 114.7, 94.3, 71.1, 64.9, 55.7, 48.2, 35.8.
+
HRMS (ESI+) calculated for C30
527.1334; found 527.1333.
2 2
H28BrN O (M+H )
6
-(4-chlorophenyl)-2,3,5-triphenylhexahydro-2H-
pyrrolo[3,2-d]isoxazole (3c) [dr = 50:50]: yield: 37 mg
o
1
(
54%); white solid; mp 113.0-116.0 C; H NMR (400
MHz, Chloroform-d) δ 7.50 (d, J = 7.7 Hz, 2H), 7.35 (tt, J
16.8, 7.4 Hz, 9H), 7.25 – 7.18 (m, 5H), 7.13 (d, J = 8.8
Hz, 6H), 7.01 (q, J = 7.4 Hz, 7H), 6.95 – 6.84 (m, 3H),
.72 (t, J = 9.1 Hz, 4H), 6.26 (d, J = 5.9 Hz, 1H), 6.20 (d, J
3
-(2-bromophenyl)-6-(4-methoxyphenyl)-2,5-diphen-
yl-hexahydro-2H-pyrrolo[3,2-d]isoxazole (3f'): yield: 42
=
o
1
mg (53%); yellow solid; mp 160.3-164.0 C; H NMR (400
MHz, Chloroform-d) δ 7.85 (dd, J = 7.8, 1.7 Hz, 1H), 7.57
6
(
dd, J = 8.0, 1.2 Hz, 1H), 7.35 (td, J = 7.6, 1.3 Hz, 1H),
=
5.4 Hz, 0.9H), 5.02 (d, J = 7.9 Hz, 0.9H), 4.88 (dd, J =
2.2, 7.8 Hz, 1.9H), 4.81 (s, 1H), 3.67 – 3.57 (m, 0.9H),
.45 (q, J = 8.1 Hz, 1H), 2.58 (td, J = 10.7, 10.3, 5.1 Hz,
7
3
1
.25 – 7.12 (m, 6H), 7.00 – 6.94 (m, 2H), 6.92 – 6.83 (m,
H), 6.81 – 6.66 (m, 4H), 6.21 (d, J = 5.9 Hz, 1H), 5.19 (s,
H), 4.72 (dd, J = 8.1, 3.2 Hz, 1H), 3.73 (s, 3H), 3.38 (td, J
1
3
7
This article is protected by copyright. All rights reserved.

Advanced Synthesis & Catalysis
10.1002/adsc.201701476
=
8.2, 5.6 Hz, 1H), 2.59 (dt, J = 12.9, 8.2 Hz, 1H), 2.22
3,5-bis(2-bromophenyl)-2,6-diphenylhexahydro-2H-
pyrrolo[3,2-d]isoxazole (3j) [dr = 25:75]: yield: 62 mg
(72%); white solid; mp 62.8-66.0 C; H NMR (400 MHz,
Chloroform-d) δ 7.87 (dd, J = 7.8, 1.7 Hz, 1H), 7.78 (d, J =
7.7 Hz, 0.22H), 7.60 – 7.53 (m, 2.44H), 7.36 (t, J = 7.4 Hz,
1.22H), 7.29 (d, J = 8.0 Hz, 1H), 7.24 – 7.13 (m, 6H), 7.09
– 7.02 (m, 2.44H), 7.00 – 6.85 (m, 4H), 6.82 (t, J = 7.2 Hz,
1
3
(
ddd, J = 12.6, 9.0, 3.2 Hz, 1H). C NMR (101 MHz,
) δ 152.6, 151.0, 143.1, 140.4, 138.1, 132.8, 129.1,
28.91, 128.90, 128.8, 128.0, 127.0, 125.7, 122.6, 121.1,
16.3, 114.6, 114.1, 95.6, 74.3, 64.1, 55.7, 53.8, 40.4.
o
1
CDCl
3
1
1
+
HRMS (ESI+) calculated for C30
H
28BrN
2
O
2
(M+H )
5
27.1334; found 527.1330.
1
6
1
0
H), 6.72 (d, J = 7.9 Hz, 4H), 6.33 (d, J = 5.2 Hz, 0.22H),
.26 (d, J = 5.9 Hz, 1H), 5.33 – 5.29 (m, 0.22H), 5.21 (s,
.22H), 5.15 (d, J = 8.2 Hz, 1H), 3.88 (p, J = 8.0 Hz,
.22H), 3.33 (td, J = 9.0, 5.9 Hz, 1H), 2.65 (dt, J = 13.1,
3
-(2-bromophenyl)-6-(naphthalen-2-yl)-2,5-diphenyl-
hexahydro-2H-pyrrolo[3,2-d]isoxazole (3g) [dr
7:73]: yield: 31 mg (38%); yellow solid; mp 197.9-201.6
=
2
o
1
8.8 Hz, 1H), 2.45 (dt, J = 13.0, 8.7 Hz, 0.22H), 2.29 (ddd,
J = 12.0, 9.1, 2.1 Hz, 1H), 1.49 (dd, J = 13.3, 9.3 Hz,
C; H NMR (400 MHz, Chloroform-d) δ 7.93 (dd, J = 7.8,
1
.7 Hz, 1H), 7.79 (dd, J = 7.8, 1.7 Hz, 0.5H), 7.74 – 7.67
13
0
1
1
1
1
1
3
3
.22H). C NMR (101 MHz, CDCl ) δ 150.9, 150.8, 143.6,
(
m, 3H), 7.64 – 7.54 (m, 3H), 7.43 – 7.27 (m, 6H), 7.26 –
40.7, 140.5, 140.1, 137.5, 133.6, 133.5, 132.8, 130.1,
29.4, 129.2, 129.2, 129.1, 129.0, 128.9, 128.8, 128.7,
28.1, 128.0, 127.9, 127.8, 127.0, 126.8, 122.6, 122.3,
22.3, 122.2, 121.3, 118.9, 118.8, 115.5, 115.0, 114.9,
7
6
.07 (m, 13H), 7.07 – 6.97 (m, 5H), 6.97 – 6.92 (m, 2H),
.89 – 6.84 (m, 1H), 6.41 (d, J = 5.4 Hz, 0.5H), 6.37 (d, J
=
6.0 Hz, 1H), 5.26 (d, J = 4.6 Hz, 1.5H), 5.15 (dd, J = 8.0,
2
.6 Hz, 0.5H), 4.97 (dd, J = 8.3, 2.6 Hz, 1H), 4.06 – 3.92
m, 0.5H), 3.46 (td, J = 8.7, 5.8 Hz, 1H), 2.65 (dt, J = 12.9,
.5 Hz, 1H), 2.45 (ddd, J = 12.6, 9.5, 8.1 Hz, 0.5H), 2.31
14.1, 95.0, 93.6, 74.1, 70.8, 64.3, 63.8, 53.6, 48.2, 38.0,
(
+
3.5. HRMS (ESI+) calculated for C29
H
25Br
2
N
2
O (M+H )
8
13
575.0334; found 575.0332.
(
ddd, J = 12.8, 8.9, 2.7 Hz, 1H), 1.58 – 1.53 (m, 0.5H). C
NMR (101 MHz, CDCl ) δ 151.2, 150.7, 142.7, 142.4,
41.9, 141.9, 140.2, 137.7, 134.7, 134.6, 132.9, 132.8,
3
1
1
1
1
1
1
6
3-(2-bromophenyl)-6-(4-fluorophenyl)-5-(naphthalen
-1-yl)-2-phenylhexahydro-2H-pyrrolo[3,2-d]isoxazole
(3k) [dr = 25:75]: yield: 74 mg (87%); white solid; mp
30.0, 129.37, 129.36, 129.2, 129.1, 128.99, 128.96,
28.95, 128.94, 128.91, 128.86, 128.8, 128.1, 127.8, 127.8,
27.8, 127.6, 127.2, 127.1, 126.72, 126.67, 126.27, 126.26,
25.7, 125.6, 122.9, 122.6, 122.4, 122.3, 121.2, 117.5,
17.3, 115.7, 114.1, 110.0, 109.8, 95.3, 93.7, 74.4, 70.9,
o
1
90.6-93.7 C; H NMR (400 MHz, Chloroform-d) δ 7.90 –
7.80 (m, 4H), 7.69 (d, J = 8.4 Hz, 1H), 7.52 (ddd, J = 12.2,
7.2, 2.3 Hz, 5H), 7.40 – 7.26 (m, 3H), 7.18 (dtd, J = 21.1,
7.5, 1.4 Hz, 4H), 6.98 (ddt, J = 7.1, 2.2, 1.0 Hz, 3H), 6.95
– 6.82 (m, 5H), 6.72 – 6.65 (m, 3H), 6.33 (d, J = 5.2 Hz,
4.9, 64.2, 53.9, 48.3, 40.0, 35.7. HRMS (ESI+) calculated
+
for C33
H
28BrN
2
O (M+H ) 547.1385; found 547.1383.
0
0
1
.26H), 6.27 (d, J = 5.9 Hz, 1H), 5.71 (d, J = 7.7 Hz,
.26H), 5.56 (d, J = 8.2 Hz, 1H), 5.23 (d, J = 5.0 Hz,
.26H), 4.02 – 3.85 (m, 0.26H), 3.38 (td, J = 8.9, 5.8 Hz,
3
-(2-bromophenyl)-2,6-diphenyl-5-(p-tolyl)hexa-
hydro-2H-pyrrolo[3,2-d]isoxazole (3h) [dr = 27:73]:
o
1
1H), 2.75 (dt, J = 12.6, 8.8 Hz, 1H), 2.63 – 2.56 (m,
yield: 49 mg (64%); yellow solid; mp 73.3-78.5 C; H
0
.26H), 2.38 (ddd, J = 12.7, 8.9, 2.2 Hz, 1H), 1.58 – 1.54
NMR (400 MHz, Chloroform-d) δ 7.87 (dd, J = 7.9, 1.7 Hz,
13
(
m, 0.26H). C NMR (101 MHz, CDCl
3
) δ 157.7, 155.3,
1
4
H), 7.78 (dd, J = 7.8, 1.7 Hz, 0.25H), 7.56 (ddd, J = 8.1,
.8, 1.2 Hz, 1.25H), 7.35 (td, J = 7.7, 1.3 Hz, 1H), 7.28 (dd,
1
=
51.2, 150.8, 140.3, 140.0, 137.6, 136.2, 136.1, 134.4 (d, J
2.7 Hz), 132.9, 132.8, 130.4, 130.3, 129.9, 129.4, 129.3,
J = 8.7, 7.2 Hz, 1H), 7.17 (dtd, J = 18.2, 8.7, 7.9, 4.7 Hz,
1
1
1
1
4
29.2, 129.13, 129.07, 128.8, 128.0, 127.8, 127.8, 126.34,
26.27, 126.1, 125.9, 125.8, 125.7, 125.6, 125.5, 122.9,
22.8, 122.6, 122.4, 122.3, 121.3, 115.8, 115.8, 115.7,
15.6, 115.5, 114.1, 95.4, 93.9, 74.1, 70.8, 61.8, 61.2, 54.2,
7
H), 7.07 – 6.96 (m, 4H), 6.92 (t, J = 6.2 Hz, 3H), 6.85 (d,
J = 7.7 Hz, 3H), 6.80 (d, J = 7.9 Hz, 4H), 6.25 (d, J = 5.2
Hz, 0.25H), 6.21 (d, J = 6.0 Hz, 1H), 5.27 – 5.23 (m,
0
8
3
1
3
.25H), 5.18 (s, 1H), 5.04 – 4.94 (m, 0.25H), 4.81 (dd, J =
.2, 2.3 Hz, 1H), 3.91 (dtd, J = 10.2, 7.7, 5.1 Hz, 0.25H),
.38 (td, J = 8.9, 5.9 Hz, 1H), 2.58 (dt, J = 12.8, 8.6 Hz,
H), 2.40 (dt, J = 10.4, 2.2 Hz, 0.25H), 2.27 (d, J = 8.3 Hz,
.75H), 2.24 – 2.19 (m, 1H), 1.45 (ddd, J = 10.4, 7.0, 1.7
8.9, 38.6, 34.2. HRMS (ESI+) calculated for
+
C
33
H
27BrFN
2
O (M+H ) 565.1291; found 565.1288.
3-(2-bromophenyl)-2,6-diphenyl-5-((E)-styryl)-hexa-
hydro-2H-pyrrolo[3,2-d]isoxazole (3l) [3l/3l'= 28:72]:
13
3
Hz, 0.25H). C NMR (101 MHz, CDCl ) δ 151.2, 151.1,
o
1
1
1
1
1
7
44.1, 140.3, 139.8, 139.4, 137.9, 136.7, 136.6, 132.8,
yield: 15 mg (19%); yellow solid; mp 177.5-180.5 C; H
NMR (400 MHz, Chloroform-d) δ 7.69 (dd, J = 7.8, 1.7 Hz,
1H), 7.53 (dd, J = 8.0, 1.3 Hz, 1H), 7.27 – 7.15 (m, 10H),
7.15 – 7.08 (m, 2H), 6.96 – 6.85 (m, 5H), 6.79 – 6.71 (m,
1H), 6.27 (dd, J = 16.0, 1.1 Hz, 1H), 6.08 – 5.90 (m, 2H),
5.16 (d, J = 7.6 Hz, 1H), 4.54 (tt, J = 6.1, 1.7 Hz, 1H), 3.90
(dtd, J = 10.0, 7.8, 5.2 Hz, 1H), 2.13 (ddd, J = 12.5, 10.0,
29.9, 129.6, 129.6, 129.3, 129.2, 129.1, 129.1, 128.9,
28.8, 128.1, 127.8, 125.6, 125.5, 122.5, 122.2, 122.1,
21.2, 118.6, 118.5, 115.1, 115.0, 114.6, 114.1, 95.0, 93.7,
4.2, 71.0, 64.7, 63.9, 53.7, 48.2, 40.0, 35.5, 29.9, 21.2.
+
HRMS (ESI+) calculated for
C
30
H
28BrN
2
O
(M+H )
5
11.1385; found 511.1380.
1
3
8
.0 Hz, 1H), 1.42 (ddd, J = 12.6, 7.9, 2.2 Hz, 1H). C
NMR (101 MHz, CDCl
3
) δ 151.1, 144.4, 137.9, 136.6,
3
-(2-bromophenyl)-5-(4-nitrophenyl)-2,6-diphenyl-
1
32.8, 130.4, 130.2, 129.9, 129.3, 129.2, 129.1, 128.7,
hexahydro-2H-pyrrolo[3,2-d]isoxazole (3i) [dr = 23:77]:
o
1
127.8, 127.7, 126.5, 122.2, 122.1, 118.7, 115.1, 114.6, 93.2,
1.1, 62.5, 48.6, 32.8. HRMS (ESI+) calculated for
yield: 75 mg (92%); yellow solid; mp 114.5-118.4 C; H
NMR (400 MHz, Chloroform-d) δ 8.10 (dd, J = 10.4, 8.6
Hz, 2.72H), 7.84 (dd, J = 7.8, 1.7 Hz, 1H), 7.75 (dd, J =
7
+
31 2
C H28BrN O (M+H ) 523.1385; found 523.1384.
7
7
7
.8, 1.7 Hz, 0.36H), 7.61 – 7.55 (m, 1.36H), 7.35 (tt, J =
.3, 1.7 Hz, 2H), 7.31 – 7.25 (m, 1H), 7.23 – 7.10 (m, 9H),
.02 – 6.93 (m, 1.36H), 6.91 – 6.79 (m, 5H), 6.77 – 6.70
3-(2-bromophenyl)-2,6-diphenyl-5-((E)-styryl)-hexa-
hydro-2H-pyrrolo[3,2-d]isoxazole (3l') [dr = 83:17]:
o
1
(
m, 3H), 6.29 (dd, J = 9.7, 5.6 Hz, 1.36H), 5.20 (d, J = 4.2
yield: 38 mg (48%); yellow solid; mp 64.6-67.9 C; H
Hz, 1.36H), 5.06 (dd, J = 8.2, 3.1 Hz, 0.36H), 4.84 (dd, J =
NMR (400 MHz, Chloroform-d) δ 7.75 (dd, J = 8.0, 4.3 Hz,
8
.4, 3.3 Hz, 1H), 3.91 (qd, J = 8.2, 5.2 Hz, 0.36H), 3.39 (td, 2H), 7.52 (d, J = 7.9 Hz, 2H), 7.27 (t, J = 7.6 Hz, 3H), 7.23
J = 8.6, 6.2 Hz, 1H), 2.70 (dt, J = 13.2, 8.3 Hz, 1H), 2.41
dt, J = 12.9, 8.7 Hz, 0.36H), 2.22 (ddd, J = 12.7, 9.0, 3.4
– 7.14 (m, 14H), 7.08 (ddd, J = 20.9, 7.5, 4.4 Hz, 12H),
7.00 (d, J = 8.1 Hz, 5H), 6.90 (d, J = 8.2 Hz, 2H), 6.80 (dq,
J = 12.7, 7.6 Hz, 7H), 6.39 (d, J = 16.0 Hz, 1H), 6.20 (d, J
= 16.0 Hz, 1H), 5.99 – 5.88 (m, 2H), 5.71 (dd, J = 16.1, 7.7
Hz, 1H), 5.64 (d, J = 6.4 Hz, 1H), 5.21 (s, 1H), 5.12 (s,
1H), 4.35 (q, J = 7.6 Hz, 2H), 3.35 (q, J = 8.3 Hz, 1H),
3.22 (q, J = 7.9 Hz, 1H), 2.61 (dt, J = 13.5, 8.6 Hz, 1H),
2.36 (dt, J = 12.9, 8.2 Hz, 1H), 2.19 (ddd, J = 12.4, 8.7, 2.9
(
13
Hz, 1H), 1.49 (ddd, J = 12.8, 8.1, 3.0 Hz, 0.36H). C NMR
101 MHz, CDCl ) δ 150.7, 150.6, 150.5, 150.4, 147.2,
(
3
1
1
1
1
7
47.2, 143.4, 143.3, 139.8, 137.4, 133.0, 132.9, 129.8,
29.5, 129.3, 129.3, 129.1, 129.0, 128.7, 128.1, 127.9,
26.6, 126.5, 124.4, 124.4, 122.5, 122.2, 121.3, 119.4,
19.3, 115.6, 115.4, 115.1, 114.1, 114.0, 94.8, 93.3, 74.1,
13
0.8, 64.0, 63.3, 53.7, 48.2, 39.9, 35.5. HRMS (ESI+)
Hz, 1H), 2.06 (dt, J = 13.6, 7.8 Hz, 1H). C NMR (101
MHz, CDCl ) δ 151.3, 151.0, 145.8, 144.5, 140.5, 140.3,
+
calculated for C29
5
H
25BrN
3
O
3
(M+H ) 542.1079; found
3
42.1075.
136.7, 136.5, 132.8, 132.6, 131.0, 130.5, 130.4, 129.2,
1
1
29.1, 128.9, 128.8, 128.6, 128.5, 128.1, 128.1, 127.7,
27.6, 126.48, 126.46, 122.6, 122.5, 121.2, 121.1, 119.3,
8
This article is protected by copyright. All rights reserved.

Advanced Synthesis & Catalysis
10.1002/adsc.201701476
1
18.6, 115.1, 115.0, 114.4, 114.1, 98.7, 94.4, 74.5, 74.1,
6.66 (d, J = 8.1 Hz, 2H), 6.21 (d, J = 5.2 Hz, 1H), 5.06 (dd,
J = 8.2, 2.7 Hz, 1H), 4.83 (d, J = 7.2 Hz, 1H), 3.51 (p, J =
7.6 Hz, 1H), 2.51 (dt, J = 12.9, 8.8 Hz, 1H), 1.42 (ddd, J =
6
3.0, 61.6, 54.7, 54.1, 37.6, 37.3. HRMS (ESI+) calculated
+
2
for C31H28BrN O (M+H ) 523.1385; found 523.1382.
13
1
1
1
1
3
2.8, 8.0, 2.7 Hz, 1H). C NMR (101 MHz, CDCl ) δ
50.5, 150.4, 147.3, 143.5, 140.2, 131.1, 130.5, 130.0,
29.4, 129.1, 126.7, 125.7, 124.4, 123.2, 123.0, 119.5,
3
-(2-bromophenyl)-6-(4-fluorophenyl)-2-phenyl-5-
(
thiophen-2-yl)hexahydro-2H-pyrrolo[3,2-d]isoxazole
3m) [dr = 31:69]: yield: 59 mg (75%); white solid; mp
16.4, 115.1, 92.9, 70.4, 63.9, 50.5, 35.9. HRMS (ESI+)
(
+
o
1
calculated for C29
H
24BrN
3
NaO
3
(M+Na ) 564.0899; found
1
41.6-145.0 C; H NMR (400 MHz, Chloroform-d) δ 7.80
5
64.0895.
(
d, J = 7.8 Hz, 1H), 7.71 (d, J = 7.8 Hz, 0.6H), 7.59 (d, J =
7
.9 Hz, 1.6H), 7.31 (dt, J = 21.3, 7.6 Hz, 3H), 7.22 – 7.05
(
m, 6H), 7.02 – 6.79 (m, 14H), 6.75 (d, J = 3.4 Hz, 0.6H),
3-(3-bromophenyl)-5-(4-nitrophenyl)-2,6-diphenyl-
6
.69 (d, J = 3.4 Hz, 1H), 6.12 (d, J = 5.4 Hz, 0.6H), 6.08 (d, hexahydro-2H-pyrrolo[3,2-d]isoxazole (3u'): yield: 29
o 1
J = 6.0 Hz, 1H), 5.20 (d, J = 7.3 Hz, 2.2H), 5.05 (dd, J =
mg (36%); yellow solid; mp 76.3-80.8 C; H NMR (400
MHz, Chloroform-d) δ 8.12 (d, J = 8.7 Hz, 2H), 7.68 (t, J
= 1.9 Hz, 1H), 7.43 (dd, J = 7.8, 1.8 Hz, 2H), 7.25 (s, 1H),
7.21 (dd, J = 8.2, 6.1 Hz, 4H), 7.15 (t, J = 7.8 Hz, 2H),
6.94 – 6.81 (m, 4H), 6.74 (d, J = 8.2 Hz, 2H), 6.34 (d, J =
5.8 Hz, 1H), 4.93 (dd, J = 8.2, 3.1 Hz, 1H), 4.81 (s, 1H),
3.40 (q, J = 7.9 Hz, 1H), 2.63 (dt, J = 12.9, 8.3 Hz, 1H),
7
3
2
7
1
1
1
1
1
1
7
.8, 2.6 Hz, 1H), 4.09 (dq, J = 15.1, 7.9, 7.2 Hz, 0.6H),
.51 (q, J = 8.1 Hz, 1H), 2.59 (dt, J = 13.2, 8.0 Hz, 1H),
.36 (ddt, J = 17.1, 12.8, 7.3 Hz, 1.6H), 1.63 (td, J = 8.6,
1
3
3
.8, 4.1 Hz, 0.6H). C NMR (101 MHz, CDCl ) δ 158.0,
58.0, 155.7, 155.6, 150.7, 150.5, 147.5, 147.4, 140.3,
40.3 (d, J = 1.9 Hz), 140.0, 137.5, 132.9, 132.9, 129.9,
29.4, 129.2, 129.1, 129.0, 128.8, 128.0, 127.8, 127.04,
27.00, 125.7, 124.2, 124.1, 123.8, 123.7, 122.64, 122.60,
22.5, 122.3, 121.2, 116.3, 116.2, 116.1, 116.0, 115.9,
15.80, 115.78, 115.57, 115.56, 114.1, 94.9, 93.4, 73.9,
13
2.14 (ddd, J = 12.4, 8.8, 3.2 Hz, 1H). C NMR (101 MHz,
3
CDCl ) δ 150.5, 150.4, 147.3, 143.3, 143.1, 131.0, 130.6,
129.8, 129.3, 129.0, 126.6, 125.3, 124.4, 123.2, 121.7,
119.5, 115.4, 114.5, 94.5, 73.9, 63.3, 54.1, 39.6. HRMS
+
0.8, 60.8, 60.0, 54.1, 48.6, 40.5, 36.1. HRMS (ESI+)
(ESI+) calculated for
564.0899; found 564.0897.
C
29
H
24BrN
3
NaO
3
(M+Na
)
+
calculated for C27
5
H
23BrFN
2
OS (M+H ) 521.0698; found
21.0695.
3
-(4-bromophenyl)-2,5,6-triphenylhexahydro-2H-
3
-(2-bromophenyl)-5-cyclohexyl-6-(4-fluorophenyl)-
pyrrolo[3,2-d]isoxazole (3v) [dr = 50:50]: yield: 37 mg
o
1
2
-phenylhexahydro-2H-pyrrolo[3,2-d]isoxazole (3n) [dr
(50%); yellow solid; mp 126.9-129.0 C; H NMR (400
MHz, Chloroform-d) δ 7.48 (dd, J = 8.1, 5.2 Hz, 3H), 7.38
(d, J = 8.1 Hz, 2H), 7.31 – 7.25 (m, 3H), 7.24 – 7.09 (m,
9H), 7.07 – 7.02 (m, 1H), 7.02 – 6.96 (m, 3H), 6.94 – 6.83
(m, 3H), 6.83 – 6.74 (m, 4H), 6.24 (dd, J = 11.6, 5.4 Hz,
1.44H), 5.05 (d, J = 8.0 Hz, 0.44H), 4.94 – 4.86 (m, 1.44H),
4.76 (s, 1H), 3.58 (q, J = 7.6, 6.7 Hz, 0.44H), 3.37 (q, J =
8.4 Hz, 1H), 2.56 (dtd, J = 13.6, 8.3, 4.3 Hz, 1.44H), 2.15
1
=
29:71]: yield: 28 mg (36%); yellow liquid; H NMR
(
7
400 MHz, Chloroform-d) δ 7.71 (dd, J = 7.8, 1.7 Hz, 1H),
.61 (dd, J = 7.8, 1.8 Hz, 0.2H), 7.54 (ddd, J = 7.9, 6.5, 1.3
Hz, 1.2H), 7.28 – 7.22 (m, 1.2H), 7.21 – 7.13 (m, 1H), 7.10
td, J = 7.7, 1.8 Hz, 1.2H), 7.02 (dd, J = 8.6, 7.3 Hz, 2H),
.98 – 6.91 (m, 2.4H), 6.90 – 6.85 (m, 0.4H), 6.83 – 6.70
m, 6H), 5.91 (d, J = 5.3 Hz, 0.2H), 5.83 (d, J = 6.1 Hz,
(
6
(
1
2
1
–
1
H), 5.09 (s, 1.2H), 3.87 – 3.78 (m, 0.4H), 3.69 (dt, J = 8.8, (ddd, J = 12.4, 8.6, 2.2 Hz, 1H), 1.49 – 1.43 (m, 0.44H).
13
.2 Hz, 1H), 3.26 (td, J = 9.2, 6.1 Hz, 1H), 2.20 (ddd, J =
3.3, 9.4, 1.9 Hz, 1H), 1.88 (dt, J = 13.3, 8.8 Hz, 1H), 1.76
1.60 (m, 3H), 1.57 – 1.50 (m, 3H), 1.42 – 1.31 (m, 2H),
3
C NMR (101 MHz, CDCl ) δ 151.0, 150.8, 144.1, 144.0,
142.6, 142.5, 140.2, 137.2, 132.0, 131.9, 129.2, 129.1,
129.0, 128.92, 128.89, 128.79, 128.5, 127.2, 125.7, 125.6,
122.5, 121.6, 121.53, 121.47, 118.7, 116.0, 115.1, 114.7,
1
3
.22 – 1.03 (m, 3H), 1.01 – 0.64 (m, 6H). C NMR (101
MHz, CDCl
3
) δ 157.6, 157.3, 155.3, 155.0, 151.2, 151.0,
114.6, 94.6, 93.2, 73.8, 70.5, 64.6, 64.1, 54.1, 50.4, 39.7,
+
1
1
1
9
3
40.6, 140.2, 138.0, 132.8, 132.8, 130.1, 129.3, 129.1,
35.9. HRMS (ESI+) calculated for C29
497.1229; found 97.1225
H
26BrN
2
O (M+H )
28.8, 128.0, 127.7, 122.7, 122.2 (d, J = 4.6 Hz), 121.0,
16.2, 116.1, 116.00, 115.96, 115.8, 115.7, 115.3, 113.9,
4.4, 93.2, 75.2, 71.6, 65.2, 64.4, 55.6, 49.6, 38.4, 37.7,
1
,5-diphenylpyrrolidin-2-one (4a): yield: 38 mg
o 1
1.0, 30.1, 29.8, 26.9, 26.6, 26.5, 26.4, 26.3, 26.1. HRMS
(
80%); yellow solid; mp 98.7-101.3 C; H NMR (400
+
(
ESI+) calculated for C29
H
31BrFN
2
O (M+H ) 521.1604;
MHz, Chloroform-d) δ 7.42 (d, J = 8.0 Hz, 2H), 7.34 –
found 521.1602.
7
4
.13 (m, 7H), 7.04 (t, J = 7.4 Hz, 1H), 5.24 (dd, J = 7.4,
.5 Hz, 1H), 2.81 – 2.69 (m, 1H), 2.68 – 2.54 (m, 2H), 1.99
13
3
-(2-chlorophenyl)-5-(4-nitrophenyl)-2,6-diphenyl-
(ddd, J = 11.8, 8.8, 5.1 Hz, 1H). C NMR (101 MHz,
hexahydro-2H-pyrrolo[3,2-d]isoxazole (3r) [dr = 29:71]:
CDCl
3
) δ 175.0, 141.4, 138.3, 129.1, 128.8, 127.8, 126.0,
o
1
yield: 76 mg (96%); yellow solid; mp 86.0-90.0 C; H
NMR (400 MHz, Chloroform-d) δ 8.01 (dd, J = 11.2, 8.7
Hz, 2.64H), 7.75 (dd, J = 7.7, 1.8 Hz, 1H), 7.69 – 7.66 (m,
125.0, 122.3, 64.0, 31.3, 29.3. HRMS (ESI+) calculated for
+
16
C H16NO (M+H ) 238.1232; found 238.1229.
0
1
–
5
8
.32H), 7.33 – 7.29 (m, 1.32H), 7.20 (dtd, J = 15.4, 7.6,
.6 Hz, 3H), 7.15 – 7.02 (m, 7H), 6.93 – 6.85 (m, 1H), 6.83
6.71 (m, 4H), 6.68 – 6.61 (m, 2.64H), 6.21 (dd, J = 7.8,
.6 Hz, 1.32H), 5.15 (d, J = 8.3 Hz, 1.32H), 4.98 (dd, J =
.3, 2.9 Hz, 0.32H), 4.75 (dd, J = 8.4, 3.3 Hz, 1H), 3.79
5
-phenyl-1-(p-tolyl)pyrrolidin-2-one (4b): yield: 40
o 1
mg (80%); white solid; mp 101.1-103.1 C; H NMR (400
MHz, Chloroform-d) δ 7.20 (d, J = 7.8 Hz, 4H), 7.17 –
7
4
(
.10 (m, 3H), 6.95 (d, J = 8.1 Hz, 2H), 5.13 (dd, J = 7.3,
.6 Hz, 1H), 2.73 – 2.61 (m, 1H), 2.60 – 2.44 (m, 2H), 2.15
(
qd, J = 8.1, 5.2 Hz, 0.32H), 3.30 (td, J = 8.5, 6.1 Hz, 1H),
13
s, 3H), 1.98 – 1.83 (m, 1H). C NMR (101 MHz, CDCl
3
)
2
0
.59 (dt, J = 13.1, 8.2 Hz, 1H), 2.33 (dt, J = 12.8, 8.7 Hz,
.32H), 2.11 (ddd, J = 12.8, 9.0, 3.4 Hz, 1H), 1.44 – 1.38
δ 174.8, 141.6, 135.8, 134.7, 129.3, 129.0, 127.8, 126.1,
22.4, 64.1, 31.2, 29.3, 20.9. HRMS (ESI+) calculated for
1
1
3
(
m, 0.32H). C NMR (101 MHz, CDCl
3
) δ 150.7, 150.6,
+
17
C H18NO (M+H ) 252.1388; found 252.1381.
1
1
1
1
1
3
50.4, 147.2, 147.2, 143.4, 143.3, 138.3, 135.8, 132.3,
32.0, 129.7, 129.6, 129.4, 129.3, 129.3, 129.2, 129.1,
29.0, 128.4, 127.5, 127.3, 126.6, 126.5, 124.4, 124.3,
22.5, 121.3, 121.3, 119.4, 119.3, 115.6, 115.4, 115.0,
14.1, 114.0, 94.8, 93.2, 71.9, 68.7, 64.0, 63.3, 53.5, 48.2,
1
-(4-methoxyphenyl)-5-phenylpyrrolidin-2-one (4c):
o 1
yield: 39 mg (73%); yellow solid, mp 82.7-84.3 C; H
NMR (400 MHz, Chloroform-d) δ 7.29 – 7.06 (m, 7H),
6
.68 (d, J = 8.5 Hz, 2H), 5.08 (dd, J = 7.4, 4.7 Hz, 1H),
3 3
9.8, 35.5. HRMS (ESI+) calculated for C29H24ClN NaO
+
3.62 (s, 3H), 2.73 – 2.60 (m, 1H), 2.59 – 2.46 (m, 2H),
(
M+Na ) 520.1404; found 520.1402.
13
1
.92 (td, J = 11.0, 8.7, 5.7 Hz, 1H). C NMR (101 MHz,
CDCl ) δ 174.8, 156.9, 141.5, 131.3, 129.0, 127.8, 126.2,
24.2, 114.0, 64.4, 55.4, 31.1, 29.2. HRMS (ESI+)
3
3
-(3-bromophenyl)-5-(4-nitrophenyl)-2,6-diphenyl-
1
hexahydro-2H-pyrrolo[3,2-d]isoxazole (3u): yield: 22
+
calculated for
68.1332.
17 2
C H18NO (M+H ) 268.1338; found
o
1
mg (27%); yellow solid; mp 66.5-70.4 C; H NMR (400
2
MHz, Chloroform-d) δ 8.06 (d, J = 8.7 Hz, 2H), 7.52 (t, J
=
7
6
1.8 Hz, 1H), 7.38 (dd, J = 7.9, 1.9 Hz, 1H), 7.29 (d, J =
.7 Hz, 1H), 7.21 (d, J = 8.1 Hz, 3H), 7.18 – 7.10 (m, 4H),
.93 (dd, J = 15.1, 7.5 Hz, 3H), 6.77 (t, J = 7.3 Hz, 1H),
1
-(4-fluorophenyl)-5-phenylpyrrolidin-2-one
(4d):
o 1
yield: 40 mg (78%); white solid; mp 92.9-95.4 C; H
9
This article is protected by copyright. All rights reserved.

Advanced Synthesis & Catalysis
10.1002/adsc.201701476
NMR (400 MHz, Chloroform-d) δ 7.25 (ddd, J = 20.0, 8.4,
5-(2-hydroxyphenyl)-1-phenylpyrrolidin-2-one (4m):
o
5
6
2
1
2
8
.4 Hz, 4H), 7.17 (d, J = 7.0 Hz, 1H), 7.15 – 7.09 (m, 2H),
.84 (t, J = 8.7 Hz, 2H), 5.11 (dd, J = 7.3, 4.9 Hz, 1H),
.74 – 2.63 (m, 1H), 2.62 – 2.47 (m, 2H), 2.03 – 1.80 (m,
yield: 25 mg (49%)； yellow solid；mp 194.8-197.0 C;
1
H NMR (400 MHz, Chloroform-d) δ 7.48 (d, J = 8.1 Hz,
2H), 7.35 – 7.18 (m, 3H), 7.06 (dt, J = 16.7, 8.2 Hz, 3H),
6.88 – 6.67 (m, 2H), 6.03 (s, 1H), 5.59 (t, J = 5.4 Hz, 1H),
2.76 (q, J = 11.3, 10.0 Hz, 1H), 2.61 (d, J = 12.7 Hz, 2H),
1
3
3
H). C NMR (101 MHz, CDCl ) δ 174.9, 159.8 (d, J =
44.7 Hz), 141.1, 134.3, 129.1, 128.0, 126.1, 124.2 (d, J =
13
.0 Hz), 115.5 (d, J = 22.4 Hz). 64.2, 31.2, 29.2. HRMS
3
2.09 (d, J = 11.2 Hz, 1H). C NMR (101 MHz, CDCl ) δ
+
(
2
ESI+) calculated for C16
H
15FNO (M+H ) 256.1138; found
175.9, 153.3, 138.3, 128.8, 127.1, 127.1, 125.1, 122.2,
56.1129.
120.8, 115.9, 59.5, 31.7, 27.1. HRMS (ESI+) calculated for
+
C
16
H
16NO
2
(M+H ) 254.1181; found 254.1174
1
-(4-chlorophenyl)-5-phenylpyrrolidin-2-one
(4e)
1
o
yield: 38 mg (70%); yellow solid; mp 83.3-85.3 C; H
5-(2-bromophenyl)-1-phenylpyrrolidin-2-one
(4n):
1
NMR (400 MHz, Chloroform-d) δ 7.30 (d, J = 8.5 Hz, 2H), yield: 48 mg (76%); yellow liquid; H NMR (400 MHz,
7
.23 (t, J = 7.4 Hz, 2H), 7.17 (d, J = 6.6 Hz, 1H), 7.11 (d, J
8.0 Hz, 4H), 5.13 (dd, J = 7.2, 4.7 Hz, 1H), 2.73 – 2.62
Chloroform-d) δ 7.61 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 8.1
Hz, 2H), 7.35 – 7.26 (m, 3H), 7.23 (t, J = 7.5 Hz, 1H), 7.12
(dt, J = 21.2, 7.1 Hz, 3H), 5.68 (d, J = 6.8 Hz, 1H), 2.70 (tq,
=
13
(
m, 1H), 2.61 – 2.46 (m, 2H), 1.97 – 1.79 (m, 1H). C
1
3
NMR (101 MHz, CDCl
3
) δ 174.9, 141.0 136.9, 130.1,
J = 19.7, 6.7 Hz, 3H), 2.01 (d, J = 10.9 Hz, 1H). C NMR
1
(
29.2, 128.8, 128.0, 125.9, 123.3, 63.9, 31.2, 29.2. HRMS
(101 MHz, CDCl
3
) δ 175.1, 139.7, 138.2, 133.5, 129.3,
+
ESI+) calculated for C16
H15ClNO (M+H ) 272.0842;
128.9, 128.1, 126.8, 124.8, 122.4, 121.2, 62.8, 31.1, 27.2.
+
found 272.0840.
HRMS (ESI+) calculated for
16.0337; found 316.0328.
16
C H15BrNO (M+H )
3
5
-phenyl-1-(4-(trifluoromethyl)phenyl)pyrrolidin-2-
1
one (4f): yield: 47 mg (77%); yellow oil; H NMR (400
MHz, Chloroform-d) δ 7.52 (d, J = 8.5 Hz, 2H), 7.41 (d, J
1,5-di-p-tolylpyrrolidin-2-one (4o): yield: 36 mg
o 1
(68%); yellow solid; mp 129.3-131.5 C; H NMR (400
MHz, Chloroform-d) δ 7.20 (d, J = 9.0 Hz, 3H), 7.03 (s,
4H), 6.97 (d, J = 8.1 Hz, 2H), 5.11 (t, J = 6.0 Hz, 1H), 2.68
(p, J = 11.4 Hz, 1H), 2.59 – 2.45 (m, 2H), 2.22 (s, 3H),
=
8.4 Hz, 2H), 7.25 (t, J = 7.4 Hz, 2H), 7.19 (d, J = 7.6 Hz,
1
1
1
H), 7.12 (d, J = 7.5 Hz, 2H), 5.21 (dd, J = 7.3, 4.3 Hz,
H), 2.76 – 2.64 (m, 1H), 2.56 (tt, J = 13.8, 8.5 Hz, 2H),
1
3
13
.95 (dq, J = 11.8, 4.2 Hz, 1H). C NMR (101 MHz,
2.17 (s, 3H), 1.91 (d, J = 12.4 Hz, 1H). C NMR (101
CDCl
3
) δ 175.3, 141.1 (d, J = 68.8 Hz), 129.4, 128.2, 126.4
3
MHz, CDCl ) δ 174.8, 138.5, 137.4, 135.7, 134.6, 129.7,
(
d, J = 32.8 Hz), 125.9 (q, J = 3.7 Hz), 125.8, 125.5, 122.8,
129.3, 126.0, 122.4, 63.9, 31.3, 29.4, 21.2, 20.9. HRMS
+
1
21.3, 63.6, 31.3, 29.3. HRMS (ESI+) calculated for
(ESI+) calculated for C18
266.1544.
H20NO (M+H ) 266.1545; found .
+
C
17
H
15
F
3
NO (M+H ) 306.1106; found 306.1102.
1
-(2-hydroxyphenyl)-5-phenylpyrrolidin-2-one (4g):
1-(4-bromophenyl)-5-(p-tolyl)pyrrolidin-2-one (4p):
o 1
o
1
yield: 28 mg (55%); Yellow solid; mp 161.9-163.2 C; H
yield: 56 mg (88%); yellow solid; mp 98.3-100.8 C; H
NMR (400 MHz, Chloroform-d) δ 7.33 (d, J = 1.6 Hz, 4H),
7.15 – 7.04 (m, 4H), 5.18 (dd, J = 7.3, 4.6 Hz, 1H), 2.74 (t,
NMR (400 MHz, Chloroform-d) δ 8.01 (s, 1H), 7.25 – 7.16
(
m, 2H), 7.16 – 7.06 (m, 3H), 7.02 – 6.90 (m, 2H), 6.83 (d,
J = 8.1 Hz, 1H), 6.71 – 6.59 (m, 1H), 5.43 – 5.32 (m, 1H),
J = 10.1 Hz, 1H), 2.67 – 2.52 (m, 2H), 2.31 (s, 3H), 1.99 (d,
1
3
13
2
.82 – 2.57 (m, 3H), 2.13 – 1.95 (m, 1H). C NMR (101
MHz, CDCl ) δ 176.9, 151.0, 140.4, 129.1, 128.1, 127.9,
26.9, 125.9, 122.7, 120.9, 120.7, 65.5, 31.3, 30.7. HRMS
J = 12.0 Hz, 1H). C NMR (101 MHz, CDCl
3
) δ 175.0,
3
137.9, 137.8, 137.5, 131.8, 129.9, 125.9, 123.6, 117.9, 63.6,
1
31.3, 29.4, 21.2. HRMS (ESI+) calculated for C17
H
17BrNO
+
+
(
ESI+) calculated for C16
54.1175.
H
16NO
2
(M+H ) 254.1181; found
(M+H ) 330.0494; found 330.0489.
2
1
-(4-fluorophenyl)-5-(4-methoxyphenyl)pyrrolidin-2-
1
1
-(naphthalen-2-yl)-5-phenylpyrrolidin-2-one (4h):
one (4q): yield: 43 mg (76%); yellow liquid; H NMR
(400 MHz, Chloroform-d) δ 7.25 (ddd, J = 7.1, 4.8, 2.5 Hz,
o
1
yield: 37 mg (64%); white solid; mp 138.4-140.5 C; H
NMR (400 MHz, Chloroform-d) δ 7.73 (d, J = 2.1 Hz, 1H), 2H), 7.03 (d, J = 8.1 Hz, 2H), 6.84 (t, J = 8.8 Hz, 2H), 6.74
7
6
.65 – 7.52 (m, 4H), 7.28 (p, J = 6.5 Hz, 2H), 7.17 (p, J =
.8, 5.8 Hz, 4H), 7.13 – 7.08 (m, 1H), 5.27 (dd, J = 7.7, 4.5
(d, J = 8.2 Hz, 2H), 5.13 – 4.97 (m, 1H), 3.67 (s, 3H), 2.65
(q, J = 10.4 Hz, 1H), 2.59 – 2.44 (m, 2H), 2.00 – 1.83 (m,
13
Hz, 1H), 2.77 – 2.64 (m, 1H), 2.62 – 2.48 (m, 2H), 1.94
3
1H). C NMR (101 MHz, CDCl ) δ 174.8, 159.8 (d, J =
1
3
(
dq, J = 9.4, 5.2 Hz, 1H). C NMR (101 MHz, CDCl
3
) δ
244.4 Hz), 159.3, 134.3 (d, J = 3.2 Hz).133.0, 127.4, 124.4
(d, J = 7.8 Hz), 115.5 (d, J = 22.6 Hz)，114.5, 63.8, 55.3,
1
1
2
2
75.1, 141.3, 135.9, 133.4, 130.9, 129.1, 128.5, 127.9,
27.5, 126.3, 126.0, 125.5, 121.5, 120.0, 64.1, 31.4, 29.3,
31.2, 29.4. HRMS (ESI+) calculated for C17
H
17FNO
2
+
+
9.3. HRMS (ESI+) calculated for C20
H
18NO (M+H )
(M+H ) 286.1243; found 286.1242.
88.1388; found . 288.1388
5
-(4-bromophenyl)-1-(4-(trifluoromethyl)phenyl)
1
-phenyl-5-(p-tolyl)pyrrolidin-2-one (4k): yield: 42
pyrrolidin-2-one (4r): yield: 45 mg (58%); yellow solid;
o
1
o 1
mg (84%); white solid; mp 116.8-119.7 C; H NMR (400
mp 97.0-99.6 C; H NMR (400 MHz, Chloroform-d) δ
7.49 (d, J = 8.7 Hz, 2H), 7.43 (d, J = 8.7 Hz, 2H), 7.41 –
7.34 (m, 2H), 7.07 – 6.93 (m, 2H), 5.18 (dd, J = 7.1, 4.6
MHz, Chloroform-d) δ 7.37 – 7.30 (m, 2H), 7.16 (td, J =
7
(
(
.4, 1.6 Hz, 2H), 7.03 (s, 4H), 7.00 – 6.93 (m, 1H), 5.14
13
dd, J = 7.6, 4.5 Hz, 1H), 2.73 – 2.61 (m, 1H), 2.59 – 2.45
Hz, 1H), 2.73 – 2.49 (m, 3H), 2.00 – 1.77 (m, 1H). C
1
3
m, 2H), 2.21 (s, 3H), 1.97 – 1.83 (m, 1H). C NMR (101
) δ 175.0, 138.4, 138.3, 137.5, 129.7, 128.7,
25.9, 124.9, 122.3, 63.8, 31.4, 29.5, 21.2. HRMS (ESI+)
3
NMR (101 MHz, CDCl ) δ 175.0, 140.4 (d, J = 129.5 Hz),
MHz, CDCl
3
132.5, 127.5, 126.6 (d, J = 33.0 Hz), 126.0 (q, J = 3.8
1
Hz).125.4, 122.7, 122.0, 121.4, 63.0, 31.2, 29.1. HRMS
+
+
calculated for
52.1387.
C
17
H
18NO (M+H ) 252.1388; found
(ESI+) calculated for C17
found 384.0204.
H
14BrF
3
NO (M+H ) 384.0211;
2
5
-(4-nitrophenyl)-1-phenylpyrrolidin-2-one
(4l):
1-(4-fluorophenyl)-5-(naphthalen-1-yl)pyrrolidin-2-
o
1
yield: 40 mg (71%); yellow solid; mp 139.0-141.0 C; H
one (4s): yield: 40 mg (66%); Yellow solid; mp 104.7-
o
1
NMR (400 MHz, Chloroform-d) δ 8.14 – 8.04 (m, 2H),
106.3 C; H NMR (400 MHz, Chloroform-d) δ 7.94 (d, J
= 8.4 Hz, 1H), 7.83 (dd, J = 7.9, 1.5 Hz, 1H), 7.69 (d, J =
8.2 Hz, 1H), 7.58 – 7.36 (m, 4H), 7.31 – 7.23 (m, 1H), 7.21
– 7.10 (m, 1H), 6.87 – 6.72 (m, 2H), 5.90 (d, J = 7.7 Hz,
7
.40 – 7.26 (m, 4H), 7.24 – 7.12 (m, 2H), 7.01 (t, J = 7.4
Hz, 1H), 5.32 (dd, J = 7.4, 5.1 Hz, 1H), 2.64 (dddd, J =
13
2
0.3, 17.9, 10.8, 4.8 Hz, 3H), 2.04 – 1.76 (m, 1H). C
1
3
NMR (101 MHz, CDCl
3
) δ 174.5, 147.6, 137.7, 129.0,
1H), 2.85 – 2.38 (m, 3H), 2.02 (q, J = 10.4 Hz, 1H).
C
1
27.0, 125.5, 124.4, 122.2, 63.1, 31.1, 28.9. HRMS (ESI+)
3
NMR (101 MHz, CDCl ) δ 175.1, 160.6, 158.2, 135.4,
+
calculated for
83.1079.
C
16
H
15
N
2
O
3
(M+H ) 283.1083; found
134.8, 134.4, 130.1, 129.5, 128.5, 126.8, 126.1, 125.5,
2
122.6, 122.3, 115.5 (d, J = 22.1 Hz), 60.5, 31.2, 27.7.
1
0
This article is protected by copyright. All rights reserved.

Advanced Synthesis & Catalysis
10.1002/adsc.201701476
20
C H
17FNO (M+H+)
HRMS (ESI+) calculated for
[
2] a) K.-V. Gothelf, K.-A. Jorgensen, Chem. Commun.
3
06.1294; found 306.1289.
2
000, 1449-1458; b) K. V. Gothelf, K. A. Jorgensen,
Chem. Rev., 1998, 98, 863-909; c) K. Hori, J. Ito, T.
Ohta, I. Furukawa, Tetrahedron. 1998, 54, 12737-
12744.
1
-(4-fluorophenyl)-5-(thiophen-2-yl)pyrrolidin-2-one
o
(
4t): yield: 27 mg (52%); white solid, mp 110.5-112.8 C;
1
H NMR (400 MHz, Chloroform-d) δ 7.24 (dd, J = 8.5, 4.7
Hz, 2H), 7.12 (d, J = 4.7 Hz, 1H), 6.89 (t, J = 8.4 Hz, 2H),
6
8
.80 (s, 2H), 5.37 (t, J = 6.0 Hz, 1H), 2.74 (dd, J = 16.9,
.0 Hz, 1H), 2.58 (h, J = 7.3 Hz, 2H), 2.11 (q, J = 7.0, 6.6
[3] a) Kanemasa, S.; Uemura, T.; Wada, E. Tetrahedron
Lett. 1992, 33, 7889-7892; b) Kanemasa, S.; Tsuruoka,
T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90; c)
Kanemasa, S.; Tsuruoka, T.; Yamamoto, H.
Tetrahedron Lett. 1995, 36, 5019; d) K.-V. Gothelf, K.-
A. Jørgensen, J. Org. Chem. 1994, 59, 5687-5691; e) C.
Palomo, M. Oiarbide, E. Arceo, J.-M.García, R. Lopez,
A. Gonzalez, A. Linden, Angew. Chem. Int. Ed. 2005,
13
Hz, 1H). C NMR (101 MHz, CDCl
3
) δ 174.1, 161.5,
1
1
C
59.1, 144.8, 133.8, 126.9, 125.5, 125.4, 125.3, 125.2,
15.8, 115.6, 60.4, 31.0, 29.5. HRMS (ESI+) calculated for
+
14
H
13FNOS (M+H ) 262.0702; found 262.0696.
5
-cyclohexyl-1-(4-fluorophenyl)pyrrolidin-2-one (4u):
o 1
yield: 35 mg (67%); white solid; mp 123.2-125.9 C; H
NMR (400 MHz, Chloroform-d) δ 7.33 (dd, J = 8.6, 4.8 Hz,
4
4, 6187-6190; f) D.-A. Evans, H.-J. Song, K.-R.
2
2
1
H), 7.09 (t, J = 8.4 Hz, 2H), 4.13 (dt, J = 8.3, 3.9 Hz, 1H),
.67 – 2.41 (m, 2H), 2.24 – 2.07 (m, 1H), 1.97 (ddt, J =
4.3, 10.1, 5.1 Hz, 1H), 1.82 – 1.44 (m, 6H), 1.27 – 0.90
Fandrick, Org. Lett. 2006, 8, 3351-3354; g) D. Chen, Z.
Wang, J. Li, Z. Yang, L. Lin, X. Liu, X. Feng, Chem.
Eur. J. 2011, 17, 5226-5229; h) Q.-Q Cheng, J.
Yedoyan, H. Arman, M.-P. Doyle, J. Am. Chem. Soc.
13
(
3
m, 5H). C NMR (101 MHz, CDCl ) δ 174.7, 161.7,
1
3
59.2, 133.79, 133.76, 126.3, 126.3, 116.1, 115.8, 64.5,
9.2, 31.6, 29.2, 26.5, 26.3, 25.8, 25.2, 19.3. HRMS
+
(
ESI+) calculated for C16
62.1598.
H
21FNO (M+H ) 262.1607; found
2
016, 138, 44-47; i) T. Kano, T. Hashimoto, K.
2
Maruoka, J. Am. Chem. Soc. 2005, 127, 11926-11927; j)
A. Sakakura, M. Hori, M. Fushimi, K. Ishihara, J. Am.
Chem. Soc. 2010, 132, 15550-15552; k) G.-H. Li, W.
Zhou, X.-X. Li, Q.-W. Bi, Z. Wang, Z.-G. Zhao, W.-X.
Hu, Z. Chen, Chem.Commun. 2013, 49, 4770-4772.
(
E)-5-styryl-1-tosylpyrrolidin-2-one (4v): yield: 49 mg
o
1
(
72%); yellow solid; mp 115.1-116.8 C; H NMR (400
MHz, Chloroform-d) δ 7.80 (d, J = 8.0 Hz, 2H), 7.31 –
7
1
1
.17 (m, 6H), 7.13 (d, J = 8.1 Hz, 2H), 6.57 (d, J = 15.7 Hz,
H), 5.93 (dd, J = 15.7, 8.2 Hz, 1H), 5.00 (t, J = 7.7 Hz,
H), 2.57 – 2.44 (m, 1H), 2.42 – 2.28 (m, 5H), 1.91 – 1.78
[
4] a) K. V. Gothelf, I. Thomsen, K. A. Jørgensen, J. Am.
Chem. Soc. 1996, 118, 59-64; b) G. Desimoni, G.
Faita, A. Mortoni, P. Righetti, Tetrahedron Lett. 1999,
40, 2001-2004; c) S. Kobayashi, Kawamura, M. J. Am.
Chem. Soc. 1998, 120, 5840-5841; d) K. Hori, H.
Kodama, T. Ohta, I. Furukawa, J. Org. Chem. 1999,
64, 5017-5023; e) S. Kanemasa, Y. Oderaotoshi, J.
Tanaka, E. Wada, J. Am. Chem. Soc. 1998, 120,
13
(
3
m, 1H). C NMR (101 MHz, CDCl ) δ 173.1, 145.0,
1
1
36.0, 135.7, 133.2, 129.5, 128.8, 128.7, 128.4, 126.7,
26.4, 62.0, 30.8, 26.1, 21.7. HRMS (ESI+) calculated for
+
C
19
H
20NO
3
S (M+H ) 342.1164; found 342.1161.
Acknowledgements
We are grateful for financial support from the National
Natural Science Foundation of China (grants 21372120) and
Tianjin Natural Science Foundation of China (17JCZDJC37300)
as well as the National Key Research and Development Program
of China (2017YFD0201404) for this work. And we also thank
the support from the Collaborative Innovation Center of
Chemical Science and Engineering (Tianjin).
1
2355-12356; f) S. Iwasa, S. Tsushima, T. Shimada, H.
Nishiyama, Tetrahedron 2002, 58, 227-232; g) J. P.
G.Seerden, M. M. M. Boeren, H. W. Scheeren,
Tetrahedron 1997, 53, 11843-11852; h) K. B.
Simonsen, P. Bayon, R. G. Hazell, K. V. Gothelf,
Jørgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-
3
853; i) K.-B. Jensen, R.-G. Hazell, K.-A. Jørgensen,
J. Org. Chem. 1999, 64, 2353-2360.
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26 2
9] Crystal data for the compound endo-3a: C29H N O,
MW) 418.52, Monoclinic, P2
I>2ó(I)], R1) 0.0824, wR2) 0.1985, R indices (all
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=
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[
1
2
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Advanced Synthesis & Catalysis
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FULL PAPER
The catalysts-controlled divergent cascade
reactions of homopropargylic amines and nitrones:
Synthesis of pyrroloisoxazolidines and γ-lactams
Adv. Synth. Catal. Year, Volume, Page – Page
Yuanfang Kong, Yingze Liu, Boyi Wang, Shengli
Li, Lingyan Liu*, Weixing Chang, Jing Li*
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