Iron-Mediated Cyanoalkylsulfonylation/Arylation of Active Alkenes with Cycloketone Oxime Derivatives via Sulfur Dioxide Insertion

Article abstract of DOI:10.1002/adsc.202000369

Iron-mediated radical cyanoalkylsulfonylation/arylation of active olefins with cycloketone oxime derivatives via cleavage of C?C single bond and insertion of SO₂ is developed for the preparation of cyanoalkylsulfonylated oxindoles. This difunctionalization of carbon?carbon double bond via a radical pathway involves cyclobutanone oxime ester fragmentation, sulfonyl radical generation and radical addition/5-exo cyclization. The methodology displays good functional group tolerance and does not require any external bases or oxidants. (Figure presented.).

Full text of DOI:10.1002/adsc.202000369

Title: Iron-Mediated Cyanoalkylsulfonylation/Arylation of Active Alkenes
with Cycloketone Oxime Derivatives via Sulfur Dioxide Insertion
Authors: Zan Chen, Quan Zhou, Qiao-Lin Wang, Pu Chen, Biquan
Xiong, Yun Liang, Kewen Tang, and Yu Liu
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
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to this Accepted Article as a result of editing. Readers should obtain
the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Adv. Synth. Catal. 10.1002/adsc.202000369
Link to VoR: https://doi.org/10.1002/adsc.202000369

Advanced Synthesis & Catalysis
10.1002/adsc.202000369
UPDATE
DOI: 10.1002/adsc.200((will be filled in by the editorial staff))
Iron-Mediated Cyanoalkylsulfonylation/Arylation of Active
Alkenes with Cycloketone Oxime Derivatives via Sulfur Dioxide
Insertion
†
a
†a
a
a
a
*b
Zan Chen, Quan Zhou, Qiao-Lin Wang, Pu Chen, Bi-Quan Xiong, Yun Liang,
a
*ab
Ke-Wen Tang, Yu Liu
a
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan
14006, China.
4
b
Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal
University, Changsha, Hunan 410081, China.
[
Phone and fax number: +86073-0864-0122 and E-mail addresses: liuyu@hnist.edu.cn (Yu Liu) and yliang@hunnu.edu.cn
(
Yun Liang)]
†
These authors contributed equally to this work
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.200######.((Please
delete if not appropriate))
radical groups,[10]
including
and
esters,
[17f]
amides,[17f]
Thus, the
Abstract.
Iron-mediated
[17f]
[19e]
cyanoalkylsulfonylation/arylation of active olefins with carboxyls
tetrazoles.
cycloketone oxime derivatives via cleavage of C–C single development of convenient and efficient methods for
bond and insertion of SO is developed for the preparation the preparation of alkylnitriles has garnered
of cyanoalkylsulfonylated
2
oxindoles.
This increasing
attention.
The
dehydration
of
or
[11a-d]
[11e-g]
[12d-g]
difunctionalization of carbon–carbon double bond via a
radical pathway involves cyclobutanone oxime ester
fragmentation, sulfonyl radical generation and radical
addition/5-exo cyclization. The methodology displays good
functional group tolerance and does not require any
external bases or oxidants.
aldoximes,
dehydrogenation of amines,
[12a-c]
amides
and cyanation of alkyl halides
are
typical methods for the construction of alkylnitriles.
Alkylnitrile derivatives can be obtained from general
3
alkylnitriles via functionalization of their α-C(sp )–H
[13]
bonds. Additionally, the cleavage of σ-C–C bonds
in cyclobutanone oxime esters has been employed as
an efficient approach to introduce cyanoalkyl groups
Keywords: insertion of sulfur dioxide; cycloketone oxime
esters; iron-mediated; oxindoles; acrylamides
[14-17]
[14a]
into organic molecules.
Zard and co-workers
reported the first radical σ-C–C bond
Sulfur-containing organic compounds are essential
synthetic intermediates in pharmaceutical and organic
syntheses.[
1-2]
Sulfones are widely utilized in
pharmaceuticals, agrochemicals, organic syntheses,
flame-retardant materials, and the materials
industry.[ Thus, the development of convenient and
efficient protocols for the synthesis of sulfones is of
significant interest to chemists.[ In recent years,
numerous methods have been developed for the
construction of various sulfones.[ In these methods,
3-4]
5]
6]
Scheme 1. Selected reactions for radical carbon–carbon
bond cleavage of cycloketone oxime derivatives
the insertion of SO
2
is a straightforward and
convenient pathway for the preparation of sulfones.
[
7a-c]
[7d-
Among them, thiourea dioxide,
sodium sulfites,
g]
[8]
and DABCO·(SO
2
) [DABSO] are commonly
employed as SO sources to access sulfones.
2
cleavage of S-aryl sulphenylimines for the synthesis
[7-8]
2
of alkylnitriles. Subsequently, numerous researchers,
Alkylnitrile derivatives are a class of important
synthons that exist in numerous natural products and
pharmaceuticals.[ Moreover, cyanoalkyl groups can
be readily converted to other useful functional
[14b-c]
[14d-e]
[15a-e]
including Selander,
Uemura,
Xiao,
[16a-d]
[16e]
Wu,[16f] Li[16g] and other groups
have developed analogous C–C bond cleavages of
cycloketone oximes. These strategies utilize
[17]
Guo,
Yu,
9]
1
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Advanced Synthesis & Catalysis
10.1002/adsc.202000369
cyanoalkyl radicals generated from the C–C bond with cycloketone oxime esters for the construction of
cleavage of cycloketone oximes in coupling reactions cyanoalkylsulfonylated oxindoles through the
[15a]
with other substrates. In 2018, Xiao and Chen
reported the visible-light-induced copper-catalyzed γ-
insertion of SO
2
(Scheme 2b).
We commenced our study by optimizing reaction
cyanoalkylation/arylation of styrenes with oxime conditions for the cyanoalkylsulfonylation/arylation
esters and aryl boronic acids for the preparation of between N-methyl-N-phenylmethacrylamide 1a and
alkylnitrile-containing 1,1-diarylmethanes (path I, cyclobutanone O-(4-(trifluoromethyl)benzoyl) oxime
[15e]
Scheme 1). In the same year, their group
2a (Table 1). The cyanoalkylsulfonylated oxindole
developed an analogous visible-light-mediated cross- 3aa was produced in 62% yield when this reaction
coupling of alkenes with cyanoalkyl radicals (path II,
Scheme 1). However, methods that employ Table 1. Screening of optimal reaction conditions.[a]
cyanoalkyl radicals to capture CO, O
2
or SO are
2
scarce. Lu’s group[ described the capture of sulfur
dioxide in the reaction of oxime esters with
trifluromethylsulfones or vinyl triflates to access
17a]
allylsulfones and β-ketosulfones (path III, Scheme 1).
Wu and Ye[
17b]
presented the photoredox-mediated
cyanoalkylsulfonylation/alkoxylation of alkenes with
oxime esters, K and alcohols or water for the
synthesis of β-alkoxy or β-hydroxyl sulfones (path IV,
2
S
2
O
5
Isolated
Entry Variation from the standard conditions
[17c]
yield (%)
Scheme 1). Wu and co-workers
disclosed the
1
2
3
4
5
none
2a-1 instead of 2a
a-2 instead of 2a
2a-3 instead of 2a
2a-4 instead of 2a
62
37
23
46
20
0
carbonylative coupling of styrylboronic acids with
oxime esters under catalyst-free conditions (path V,
[
17d]
2
Scheme 1). Yu and co-workers
developed the
of
copper-catalyzed cyanoalkoxylation
polysubstituted olefins with cycloketone oxime
derivatives via the insertion of oxygen (path VI,
Scheme 1). Recently, our group reported the dual
ring-opening of MCPs and cyclobutanone oximes for
the generation of 2-cyanoalkylsulfonylated 3,4-
[b]
6
without FeCl
2
7
8
9
Fe(OAc)
2
instead of FeCl
2
31
18
26
20
51
44
12
51
61
40
37
24
60
30
0
Fe(OTf)
Fe(acac)
2
instead of FeCl
instead of FeCl
2
2
2
dihydronaphthalene derivatives via the insertion of
(Scheme 2a).[
17i]
10
FeCl
CuCl instead of FeCl2
Cu O instead of FeCl
AgNO instead of FeCl
Ru(bpy) Cl instead of FeCl
FeCl (20 mol %)
instead of K
thiourea dioxide instead of K
DABSO instead of K
(3 equiv)
DCE instead of CH
THF instead of CH
3 2
instead of FeCl
SO
2
However, a disadvantage of the
2
-trapping strategies [
17a,b,i]
1
1
above-mentioned SO
is the
high cost of photocatalysts.
12
2
2
1
1
3
3
2
4[
c]
3
2
2
1
1
1
1
1
2
5
6
7
8
9
0
2
Na
2
S
2
O
5
2 2 5
S O
2
S
2
O
5
S
2 2
O
5
2 2 5
K S O
3
CN
CN
2
1[
d]
3
2
2
toluene instead of CH
DMF instead of CH CN
CN
3
CN
34
0
0
41
50
43
63
52
Scheme 2. Difunctionalization of active olefins with
cycloketone oxime esters via the insertion of SO
[
d]
2
2
3
4
3
2
[
d]
DMSO instead of CH
3
t
2
5
6
7
8
AcO Bu
o
Oxindoles are highly important structural motifs
and synthetic intermediates encountered in numerous
at 60 C
2
2
2
o
at 100 C
[18]
drugs and natural products.
Owing to their
for 48 h
none
extensive applications, many organic chemists have
devoted their attention to developing new methods for
the preparation of oxindoles. In recent years, a series
of strategies for the construction of oxindoles via
9[
e]
2
[
a]
Reaction conditions: 1a (0.2 mmol, 0.1 M), 2a (0.3
mmol, 1.5 equiv), FeCl (2.6 mg, 10 mol %), K
88.8 mg, 2 equiv) and CH
2
2 2 5
S O
o
(
3
CN (2 mL) at 80 C (oil
oxidative radical coupling (ORC) have been
bath) in an argon atmosphere for 12 h.
developed.[
19-20]
In 2017, Wu and co-workers reported
[
[
[
[
b]
c]
d]
e]
Majority of 1a was recovered.
Under 5 W blue LED irradiation
Majority of 1a was decomposed.
the synthesis of oxindole derivatives via
arylsulfonylarylation of activated alkenes using
20d]
DABCO•(SO
2 2
)
and aromatic amines.[
Herein, we
1
a (1g, 5.71 mmol) and solvent (30 mL) for 60 h.
present
an
iron-catalyzed
cyanoalkylsulfonylation/arylation of active olefins
2
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Advanced Synthesis & Catalysis
10.1002/adsc.202000369
was performed in the presence of FeCl
2
(2.6 mg, 10 did not deliver the corresponding target product
mol %), K
2
o
S
2
O
5
(88.8 mg, 2 equiv) and CH CN (2 3fa–ga. We then explored the tolerability of the
3
mL) at 80 C (oil bath) for 12 h (entry 1). Next, a substituents on the N-aryl moiety. 4-Substituted
variety of substituted cyclobutanone oxime esters 2 acrylamides bearing substituents at the para-
were tested. The results indicated that position on the aryl ring were also examined. The
cyclobutanone oxime esters 2a-1−2a-4, namely yields indicated that the electronic properties of the
cyclobutanone O-(4-nitrobenzoyl) oxime 2a-1, substituent groups had a significant effect, whereby
cyclobutanone O-(4-fluorobenzoyl) oxime 2a-2, substrates
bearing
electron-withdrawing
cyclobutanone O-perfluorobenzoyl oxime 2a-3, and substituents were less reactive than those with
cyclobutanone O-benzoyl oxime 2a-4, were all electron-donating ones (products 3ha–qa). Due to
suitable for this transformation. However, all the strong electron-withdrawing nature of the NO
afforded lower yields than oxime ester 2a (entries moiety, 1r could not react with oxime ester 2a
–5). The iron catalyst was indispensable for this (product 3ra). Derivative 1s bearing a MeO group
transformation and the target product 3aa could not at the meta-position on the aryl ring furnished two
be obtained in the absence of FeCl (entry 6). Based isomers, 3sa and 3sa’ in a ratio of 4 : 5. Two
on these experimental results, a series of other isomers, 3ta and 3ta’, in a ratio of 2 : 3 were
metal salts, such as Fe(OAc) , Fe(OTf) , Fe(acac) similarly obtained from 1t.
FeCl , CuCl, Cu O and AgNO , were screened.
2
2
2
2
2
2
,
3
2
3
However, none of these metal salts could afford Table 2. The scope of active alkenes (1) and cycloketone
oxime esters (2).[
a]
higher yields than FeCl
2
(entries 7–13).
Additionally, the desired product 3aa could be
obtained in 51% yield when this reaction was
conducted in the presence of Ru(bpy)
3
17i]
Cl
2
under 5
Increasing
to 20 mol% did not increase
the reaction yield (entry 15). Next, a series of sulfur
[
W blue LED irradiation (entry 14).
the amount of FeCl
2
dioxide sources, including Na
dioxide and DABSO [DABCO·(SO
2
S
2
O
5
,
thiourea
], were
2 2
)
examined. The results revealed that K
afforded optimal results (entries 16–18). Using 3
equiv of in the reaction furnished
cyanoalkylsulfonylated oxindole 3aa in 60% yield
2
S
2
O
5
K
2
S
2
O
5
(
entry 19). Subsequently, several common solvents,
such as DCE, THF, toluene, DMF, DMSO and
t
AcO Bu were tested (entries 20–25). Only DCE,
toluene and AcO Bu afforded the target product in
t
relatively low yields. Varying the reaction
temperature (entries 26–27) and prolonging the
reaction time to 48 h (entry 28) did not lead to
improved results. A gram-scale experiment, which
was conducted in the presence of acrylamide 1a (1
o
g, 5.71 mmol) and MeCN (30 mL) at 80 C for 60 h,
produced the cyanoalkylsulfonylated oxindole 3aa
in 52% yield (entry 29).
Based on the optimal reaction conditions, we
studied the substrate scope of acrylamides 1 and
cyclobutanone oxime esters 2 (Table 2). 3-
Substituted cyclobutanone oxime esters 2b–e
bearing aryl, benzyloxy and ester groups gave the
corresponding products 3ab–ae in 44-51% yields.
Oxetan-3-one-derived O-acyl oxime 2f underwent
the cyanoalkylsulfonylation/arylation smoothly and
provided the final product 3af in 55% yield. The
scope of acrylamides 1 was then investigated in the
presence of 2a, FeCl
2
, K
2
S
2
O
5
, and CH CN.
3
Acrylamides in which the N-methyl group was
replaced by an aryl (1b), benzyl (1c) or substituted
benzyl (1d–e) groups, were compatible with the
[
a]
Reaction conditions: 1 (0.2 mmol, 0.1 M), 2 (0.3 mmol,
.5 equiv), FeCl (2.6 mg, 10 mol %), K (88.8 mg, 2
the equiv) and CH CN (2 mL) at 80 C (oil bath) under an
1
2
2 2 5
S O
o
reaction
corresponding cyanoalkylsulfonylated oxindoles
ba–ea in 43%-66% yields. However, acrylamides
bearing an N-H group (1f) or an N-Ac group (1g)
conditions
and
assembled
3
argon atmosphere for 12 h; The major diastereomer is
shown with the dr value given in parentheses.
3
[
b]
Majority of starting material 1 was recovered.
3
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Advanced Synthesis & Catalysis
10.1002/adsc.202000369
2
-Substituted acrylamide 1u was not suitable for
According to the literature[14-20] and experimental
this reaction, as the steric hindrance of the methyl results, we have proposed a mechanism for the
group impeded the reaction, and 1u was largely iron-mediated radical
recovered at the end of the process (product 3ua). cyanoalkylsulfonylation/arylation of active olefins
These conditions were successfully applied to the with cycloketone oxime esters and K (Scheme
2
S
2
O
5
cyanoalkylsulfonylation/arylation of N-methyl-N- 4). Initially, oxime ester 2a undergoes SET
(
naphthalen-1-yl)methacrylamide 1v to yield reduction by Fe(II) to generate the iminyl radical
[
16d]
product 3va. Acrylamides in which the methyl A,
in which cleavage of the C–C bond produces
[
14-17]
group at the 2-position of substrate 1a was replaced intermediate B.
by either a Bn group or a CH
tolerated (products 3wa–xa).
Next, intermediate B could
, generated from K , to provide
1,1-Diphenylethene could trap
2
OAc group, were well trap SO
2
2
S
2
O
5
[
17b,i]
To
our intermediate C.
disappointment, N-methyl-N-phenylacrylamide 1y intermediates B or C to afford the cyanoalkylated
and N-methyl-N-(2-methylallyl)aniline 1z were not product 5 and cyanoalkylsulfonylated product 6,
[
17i]
suitable candidates for the system (products 3ya– respectively. The yield of 6 was higher than 5.
za). This result suggests that the reaction of cyanoalkyl
To gain insight into the reaction mechanism, we radical B with SO occurs more rapidly than the
2
conducted several radical trapping experiments. reaction of B with 1,1-diphenylethene. Next,
The cyanoalkylsulfonylation/arylation process was intermediate C attacks the C=C bond in acrylamide
suppressed when the reactions were individually 1a to furnish intermediate D, which undergoes
performed in the presence of TEMPO, BHT or 1,1- cyclization with the intramolecular N-aryl moiety to
[
18-19]
diphenylethene (Scheme
3a–c). 4-((2,2,6,6- assemble
radical E.
Finally, radical E
Tetramethylpiperidin-1-yl)oxy)butanenitrile 4 was undergoes SET oxidation by Fe(III) and
detected by GC-MS analysis, while target product deprotonation by 4-(trifluoromethyl)benzoate ion to
3
aa was not detected when TEMPO was used in deliver product 3aa, regenerating Fe(III) to ground-
[
16d,20]
this transformation (Scheme 3a). Only 6% yield of state Fe(II).
3
aa was obtained when the reaction was conducted
in the presence of 3 equiv of BHT (Scheme 3b).
Employing 1,1-diphenylethene in this reaction
provided products 5 and 6 in 10% and 30% yields,
respectively (Scheme 3c). Subsequently, inter- and
intramolecular kinetic isotope effect experiments
were conducted under the optimal conditions. The
results suggested that this reaction did not exhibit a
kinetic isotope effect (k
H
D
/k = 1) (Scheme 3d–e).
These results collectively suggest that this reaction
involves a radical process, and that the cleavage of
2
the C(sp )–H bond on the N-aryl moiety was not a
rate-limiting step.[
18a,19b-e,20e-f]
Scheme 4. Possible Mechanism.
In conclusion, we have established a convenient
and facile pathway to diverse cyanoalkylsulfonylated
oxindoles
via
iron-mediated
radical
cyanoalkylsulfonylation/arylation of active olefins
with cycloketone oxime esters. This reaction involves
a radical pathway and consists of cyclobutanone
oxime ester fragmentation, sulfonyl radical generation
and radical addition/5-exo cyclization. Both the
cyanoalkylsulfonyl radical intermediate and the
cyanoalkyl radical intermediate could be trapped by
radical inhibitors. Further research on this sulfur
dioxide insertion strategy is currently underway in our
laboratory.
Scheme 3. Control Experiments.
4
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Advanced Synthesis & Catalysis
10.1002/adsc.202000369
Experimental Section
Timoshenko, Y.-G. Shenko, J. Sulfur Chem. 2014, 35,
1
88; e) H. Fukuda, F.-J. Frank, W.-E. Truce, J. Org.
Typical Experimental Procedure for the
Cyanoalkylsulfonylation/Arylation Reaction:
Chem. 1963, 28, 1420–1422; f) Y.-Y. Fang, Z.-G. Luo,
X.-M. Xu, RSC Adv. 2016, 6, 59661–59676; g) A.-N.-
R. Alba, X. Companyóa, R. Rios, Chem. Soc. Rev.
2010, 39, 2018–2033; (h) Y.-C. Wu, S.-S. Jiang, S.-Z.
Luo, R.-J. Song, J.-H. Li, Chem. Commun. 2019, 55,
8995–8998.
To a Schlenk tube were added acrylamides 1 (0.2
mmol, 0.1 M), cycloketone oxime esters 2 (0.3 mmol,
1
.5 equiv), FeCl
2
(2.6 mg, 10 mol %), K
CN (2 mL). Then, the reaction
was stirred at 80 C (oil bath temperature) under an
argon atmosphere for 12 until complete
2
S
2
O (88.8
8
mg, 2 equiv) and CH
3
[
[
[
4] a) W.-H. Rao, B.-B. Zhan, Chen, K. Chen, P.-X. Ling,
o
Z.-Z. Zhang, B.-F. Shi, Org. Lett. 2015, 17, 3552–
h
3
555; b) M.-J. CabreraAfonso, Z.-P. Lu, C.-B. Kelly,
consumption of the starting material was observed by
TLC and/or GC-MS analysis. Upon completion, the
reaction mixture was filtered, and the organic layer
S.-B. Lang, R. Dykstra, O. Gutierrez, G.-A. Molander,
Chem. Sci. 2018, 9, 3186–3191; c) R.-J. Song, Y. Liu,
Y.-Y. Liu, J.-H. Li, J. Org. Chem. 2011, 76, 1001–
was dried over Na
2
SO . The solvent was removed,
4
1
004; d) L.-Y. Xie, S. Peng, F. Liu, G.-R. Chen, W.
and the crude product was purified by column
chromatography (petroleum ether/ethyl acetate, 1 : 1)
to provide the desired products 3. A scaled-up
experiment conducted in the presence of acrylamide
Xia, X.-Y. Yu, W.-F. Li, Z. Cao, W.-M. He, Org.
Chem. Front. 2018, 5, 2604–2609; e) F.-H. Xiao, C.
Liu, S.-S. Yuan, H.-W. Huang, G.-J. Deng, J. Org.
Chem. 2018, 83, 10420–10429; f) B.-A. Howell, Y.-G.
Daniel, J. Fire Sci. 2018, 36, 518–534.
1
a (1.75 g, 10 mmol), cycloketone oxime ester 2a (15
mmol, 1.5 equiv), FeCl (127 mg, 10 mol %), K
4.44 g, 2 equiv) and CH
2
2
S
2
O
5
5] a) D. Zheng, J. Wu, Sulfur Dioxide Insertion
Reactions for Organic Synthesis, Nature Springer,
Berlin, 2017; (b) J.-D. Liu, L.-Y. Zheng, Adv. Synth.
Catal. 2019, 361, 1710–1732; c) S.-Q. Ye, G.-Y.-S.
Qiu, J. Wu, Chem. Commun. 2019, 55, 1013–1019; d)
G.-Y.-S. Qiu, L.-F. Lai, J. Cheng, J. Wu, Chem.
Commun. 2018, 54, 10405–10414; e) G.-Y.-S. Qiu,
K.-D. Zhou, L. Gao, J. Wu, Org. Chem. Front. 2018,
o
(
3
CN (100 mL) at 80 C under
argon atmosphere for 120 h successfully afforded the
desired product 3aa in 46% yield (1407.6 mg).
Acknowledgements
We thank the Scientific Research Fund of Hunan Provincial
Education Department (No. 18B350), the Science and Technology
Planning Project of Hunan Province (No. 2018TP1017), Natural
Science Foundation of Hunan Province (No. 2018JJ3208 and
5
, 691–705; f) J. Zhu, W.-C. Yang, X.-D. Wang, L.
Wu, Adv. Synth. Catal. 2018, 360, 386–400; g) G. Liu,
C.-B. Fan, J. Wu, Org. Biomol. Chem. 2015, 13,
2
019JJ50204) and National Natural Science Foundation of China
1
592–1599.
(
No. 21602056 and 2191061) for financial support.
6] a) Y.-C. Wu, S.-S. Jiang, S.-Z. Luo, R.-J. Song, J.-H.
Li, Chem. Commun. 2019, 55, 8995–8998; b) X.-Y.
He, X. Yue, L. Zhang, S. Wu, M. Hu, J.-H. Li, Chem.
Commun. 2019, 55, 3517–3520; c) J. Yang, Y.-Y. Liu,
R.-J. Song, Z.-H. Peng, J.-H. Li, Adv. Synth. Catal.
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UPDATE
Iron-Mediated Cyanoalkylsulfonylation/Arylation
of Active Alkenes with Cycloketone Oxime Esters
via Sulfur Dioxide Insertion
Adv. Synth. Catal. Year, Volume, Page – Page
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Chen, Bi-Quan Xiong, Yun Liang, Ke-Wen
Tang, Yu Liu
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