Syntheses of chiral ferrocenophanes and their application to asymmetric catalysis

Article abstract of DOI:10.1002/ejoc.201402985

N-Substituted 2-aza-[3]-ferrocenophanes were easily synthesized from 1,1′-ferrocenedicarbaldehyde and aliphatic amines in high yields. One of the ferrocenophanes served as a ligand for the copper-catalyzed oxidative coupling of 2-naphthol derivatives to give the products in good yields with up to 92% ee, and it also efficiently catalyzed the asymmetric Michael addition reaction as an organocatalyst.

Full text of DOI:10.1002/ejoc.201402985

SHORT COMMUNICATION
DOI: 10.1002/ejoc.201402985
Syntheses of Chiral Ferrocenophanes and Their Application to Asymmetric
Catalysis
[a]
[a]
[a]
[a]
[a]
Qiying Zhang, Xiuling Cui,* Lianmei Chen, Haitao Liu, and Yangjie Wu*
Keywords: Sandwich complexes / Organocatalysis / Asymmetric synthesis / Oxidative coupling / Michael addition
N-Substituted 2-aza-[3]-ferrocenophanes were easily synthe-
sized from 1,1Ј-ferrocenedicarbaldehyde and aliphatic
amines in high yields. One of the ferrocenophanes served
as a ligand for the copper-catalyzed oxidative coupling of 2-
naphthol derivatives to give the products in good yields with
up to 92% ee, and it also efficiently catalyzed the asymmetric
Michael addition reaction as an organocatalyst.
Introduction
Since the discovery of ferrocenophane, it has received
considerable attention[ owing to its peculiar structure, re-
activity, and wide utilizations in many areas of chemistry,
including coordination chemistry (e.g., compound I as a
1]
[
2]
chemosensor ), advanced functional materials (e.g., liquid
[
3]
crystals ), as well as medicinal chemistry (e.g., antitumor
[
4]
[5]
molecule II, antimalarial molecule III ) (Figure 1). Re-
cently, ferrocene-based ligands have played an increasingly
important role in homogeneous catalysis, especially in the
[
6]
asymmetric formation of organic target molecules. How-
ever, ferrocenophane as a ligand in asymmetric catalysis is
still less developed. To the best of our knowledge, most of
[
7]
the ferrocenophanes reported are carbon-bridged. Chiral Figure 1. Some examples of ferrocenophanes.
ferrocenophanes bearing heteroatoms in the bridge have
been rarely reported,[ largely because of the lack of gene-
7j]
[8]
ent results, we replaced the pyridyl group with a chiral pyr-
rolidine unit to synthesize novel chiral 2-aza-[3]-ferroceno-
phane amines L1 and L6 (Figure 2), which were examined
as ligands in the copper-catalyzed asymmetric oxidative
coupling of 2-naphthol derivatives and in asymmetric
Michael addition reactions.
ral and efficient protocols to build such skeletons. In our
previous work, we had reported on the synthesis and struc-
ture of N-substituted 2-aza-[3]-ferrocenophane IV in more
detail (Figure 2), and this compound was proven to be a
stable and electrochemically selective sensor for Cu2+ in the
presence of excess amounts of metal ions. The pyridyl group
was found to be essential to recognize Cu ions.
2
+
[8e]
On the other hand, the pyrrolidine group is well known
Results and Discussion
to be an important framework in transition-metal catalysis
and organocatalysis.[
6,9–13]
Particularly, pyrrolidine-based
Preparation of the Ligands
secondary amines were found to be extremely powerful in
activating carbonyl substrates through an enamine mecha-
The synthesis of 2-aza-[3]-ferrocenophane is challenging
nism in the field of organocatalysis.[ Inspired by the pres- because of its highly rigid structure. Lorkowski and Kiesel-
11]
ack first obtained N-aryl-2-aza-[3]-ferrocenophane from
1
,1Ј-ferrocenedimethanol with aryl isocyanate in only 6.7%
[
a] Henan Key Laboratory of Chemical Biology and Organic
[
8a]
Chemistry, Key Laboratory of Applied Chemistry of Henan yield. Plenio reported that N-methyl-2-aza-[3]-ferroceno-
Universities, Department of Chemistry, Zhengzhou University,
phane was prepared from [1,1Ј-ferrocenediylbis(methyl-
Zhengzhou 450052, P. R. China
ene)]bis(pyridinium) tosylate chloride in 35% yield.[ Sak-
ano also developed a procedure to N-alkyl- and N-aryl-2-
aza-[3]-ferrocenophanes in yields of 40–70% from the reac-
tion of primary amines with 1,1Ј-ferrocenedimethanol cata-
8d]
E-mail: cuixl@zzu.edu.cn
wyj@zzu.edu.cn
http://www5.zzu.edu.cn/hxxy/
Supporting information for this article is available on the
WWW under http://dx.doi.org/10.1002/ejoc.201402985.
Eur. J. Org. Chem. 2014, 7823–7829
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
7823

Q. Zhang, X. Cui, L. Chen, H. Liu, Y. Wu
SHORT COMMUNICATION
Figure 2. Strategy to design chiral ferrocenophane–amines L1 and L6.
[8b]
lyzed by RuCl (PPh ) at 180 °C.
Herein, we present a
2
3 3
mild protocol to novel chiral N-subsitituted 2-aza-[3]-ferro-
cenophanes from 1,1Ј-ferrocenedicarbaldehyde and ali-
phatic amines according to our previous work.[
8e]
Compounds 3a and 3b were synthesized according to lit-
[14]
erature procedures (Scheme 1).
forded from condensation of 1,1Ј-ferrocenedicarbaldehyde
4) with (S)-N-Boc-2-(aminomethyl)pyrrolidine (3a) (Boc =
Compound 5 was af-
(
tert-butoxycarbonyl) in dry DCE (1,2-dichloroethane) un-
der highly dilute conditions and subsequent reduction with
NaBH(OAc) (Scheme 2). The reaction was monitored by
3
thin-layer chromatography and IR spectroscopy until 1,1Ј-
ferrocenedicarbaldehyde was not detected anymore. Pure 5
was obtained in 40% yield as a yellow solid. Subsequent
Scheme 2. Syntheses of ligands L1 and L2.
treatment of 5 with 5 n HCl or LiAlH gave L1 or L2 in 99
4
or 95% yield, respectively. Compound 5 and ligands L1 and
L2 were characterized by mass spectrometry, NMR and IR
spectroscopy, and X-ray single-crystal diffraction (Fig-
ure 3). The methodology was found to be practical and ef-
ficient and featured mild (room temperature) and metal-free
reaction conditions.
Figure 3. Molecular structure of compound 5.
Scheme 1. Syntheses of compounds 3a and 3b. Cbz = benzyloxy-
carbonyl.
gave compound 10. Final diamine L5 was easily obtained
According to a similar method, compounds L3 and L4 by methylation of 10 with 37% formaldehyde and subse-
were obtained in 36% yield from the condensation of (R)- quent deprotection of the Boc group (Scheme 4). To investi-
1,1Ј-binaphthyl-2,2Ј-dicarbaldehyde (7) with the corre- gate the influence of the steric hindrance of ferrocene in
sponding chiral amines 3a and 3aЈ under the reduction of asymmetric catalysis, compound L6 was prepared. Accord-
[
17]
NaBH(OAc)3 and subsequent deprotection of the Boc ing to Marinetti’s method, intermediate 13 was obtained
group with 5 n HCl (Scheme 3). The condensation of ferro- through diastereoselective ortho-lithiation of 12 bearing 2-
cenecarbaldehyde with 3a with NaBH4 as the reductant (methoxymethyl)pyrrolidine as a chiral directing group.
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Syntheses of Chiral Ferrocenophanes
Scheme 3. Syntheses of ligands L3 and L4.
Scheme 4. Synthesis of ligand L5.
Next, the chiral auxiliaries needed removing, and this re- (Table 1, Entry 2). Ligand (S,aR)-L3 with a binaphthyl skel-
sulted in compound 14 in 83% yield. Subsequently, two eton allowed the reaction to proceed smoothly, and it pro-
consecutive steps were performed: alcoholysis and oxidative vided (S)-19a in 74% yield with 80% ee (Table 1, Entry 3).
coupling. Compound 16 was obtained in 96% yield with However, the same reaction proceeded sluggishly with the
91% ee, according to the procedure of compound L1 use of binaphthyldiamine (R,aR)-L4, which afforded the
(
Scheme 5).
product with opposite stereoselectivity in only 30% yield
with 65% ee (Table 1, Entry 4). Ring-open ferrocene deriva-
tive L5 gave 19a in 16% yield with 15% ee (Table 1, En-
try 5). Upon probing L6 with planar chirality, the reaction
gave moderate stereoselectivity with 41% ee and 77% yield
Application in the Oxidative Coupling Reaction of 2-
Naphthol Derivatives
Ligands L1–L6 were first examined as chiral ligands in (Table 1, Entry 6). Therefore, compound L1 was used as the
the Cu-catalyzed asymmetric coupling reaction of 2-naph- ligand to catalyze the asymmetric oxidative coupling of 2-
thol derivatives. Methyl 3-hydroxy-2-naphthoate (18a) was naphthol derivatives.
chosen as a model substrate in the presence of the chiral
Next, the reaction parameters were screened in the pres-
ligand (10 mol-%) and CuCl (10 mol-%) in air in aceto- ence of ligand L1 (10 mol-%). As shown in Table 2, only a
nitrile at 15 °C. The results are summarized in Table 1. The trace amount of the product was observed in the presence
desired product was obtained in 79% yield with the (S) con- of CuI, CuCl, Cu(OAc) , and Cu(OTf) (Tf = trifluoro-
2
2
figuration and 92% ee by using L1 (Table 1, Entry 1). A methylsulfonyl) in CH Cl at 50 °C (Table 2, Entries 1–4).
2
2
methyl group on the N atom of pyrrolidine hampered the We were delighted to obtain the desired product in 64%
stereoselectivity and gave only 10% ee and 32% yield yield with 85% ee by using CuCl (10 mol-%) in acetonitrile
Eur. J. Org. Chem. 2014, 7823–7829
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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7825

Q. Zhang, X. Cui, L. Chen, H. Liu, Y. Wu
SHORT COMMUNICATION
Scheme 5. Synthesis of ligand L6.
Table 1. Screening of ligands for the Cu-catalyzed asymmetric oxi- of chloroform and acetone, were found to be better than
dative coupling of methyl 3-hydroxy-2-naphthoate.
CuCl as the catalyst and acetonitrile as the solvent (Table 2,
Entries 10–26).
Under the optimized reaction conditions, the scope of
the 2-naphthol substrate was tested (Table 3). Steric hin-
drance of substituents in the γ position of 2-naphthol had
a strong impact on the yields and enantioselectivities. With
increasingly bulky substituents, the reaction gave lower
yields (Table 3, Entries 1–4). No product was obtained with
tert-butyl derivative 18d (Table 3, Entry 4). Upon introduc-
ing an aldehyde group in the γ position, compound 19e was
obtained in 35% yield with 45% ee (Table 3, Entry 5). Com-
pound 18f bearing a methoxy group in the γ position al-
lowed coordination with Cu ions, and this resulted in unex-
pected product 20p (Scheme 6). The desired product was
not observed. Compound L6 displayed a satisfactory result
for substrate 18b at 30 °C; it provided product 19b in 79%
yield with 82% ee (Table 3, Entry 6).
En-
try
Li-
gand
Yield
ee
Config.[c]
[
%][a]
[%][b]
1
2
3
4
5
6
L1
L2
L3
L4
L5
L6
79
32
74
30
16
77
92
10
80
65
15
41
(S)
(S)
(S)
(R)
(S)
(S)
[
a] Yield of isolated product. [b] Determined by HPLC analysis by
employing a Chiralpak AD column. [c] Absolute configuration was
assigned by comparison of the sign of the optical rotation with
literature data.
Application in Asymmetric Michael Addition Reactions
[
15]
With an efficient process for the asymmetric oxidative
coupling of 2-naphthol derivatives established by using li-
(
(
Table 2, Entry 5). Other copper salts such as CuI, Cu- gand L1, we then turned our attention to the asymmetric
OAc) , and Cu(OTf) did not work well (Table 2, En- Michael addition reaction via an enamine-type intermedi-
2
2
tries 6–8). The enantioselectivity was increased to 92% ee ate. We chose the conjugate addition of cyclohexanone and
by decreasing the reaction temperature to 15 °C (Table 2, β-nitrostyrene as a model reaction to examine the reaction
entry 9). No other copper salts or solvents, such as anhy- parameters in the presence of L1 or L6 (10 mol-%) and an
drous dichloromethane, methanol, acetone, and a mixture organic acid (10 mol-%) at room temperature under aerobic
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Eur. J. Org. Chem. 2014, 7823–7829

Syntheses of Chiral Ferrocenophanes
Table 2. Screening of the reaction conditions for the Cu-catalyzed
Table 3. Catalytic asymmetric oxidative coupling of 2-naphthol de-
asymmetric oxidative coupling reaction of methyl 3-hydroxy-2- rivatives.
naphthoate.
Entry Ligand R (18)
Product Yield
ee
[%]
Config.[c]
Entry Cu salt
Solvent
Temp. Yield
ee
[%]
Config.[c]
[%]
[a]
[b]
[a]
[b]
[°C]
[%]
1
2
3
4
5
L1
L1
L1
L1
L1
L6
COOMe (18a)
COOEt (18b)
COOiPr (18c)
COOtBu (18d)
CHO (18e)
19a
19b
19c
19d
19e
19b
79
73
52
trace
35
79
92
50
91
–
45
82
(S)
(S)
(S)
–
(S)
(S)
1
2
3
4
5
6
7
8
9
CuCl
CuI
Cu(OAc)
Cu(OTf)
CuCl
CuI
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
CH
2
2
2
2
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
2
3
Cl
Cl
Cl
Cl
2
2
2
2
50
50
50
50
50
50
50
50
15
15
0
0
0
–10
–10
–10
–20
–20
–30
–30
–40
–40
15
trace
trace
trace
trace
64
trace
trace
–
79
56
52
49
44
32
36
trace
32
20
46
38
19
–
–
–
–
85
–
–
–
–
–
–
(S)
–
–
2
2
[d]
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
CN
6
COOEt (18b)
[
a] Yield of isolated product. [b] Determined by HPLC analysis by
Cu(OAc)
2
employing a Chiralpak AD column. [c] Absolute configuration was
assigned by comparison of the sign of the optical rotation with
Cu(OTf)
CuCl
CuI
CuCl
CuI
Cu(OAc)
CuCl
CuI
Cu(OAc)
CuCl
CuI
CuCl
CuI
CuCl
CuI
CuCl
CuCl
CuCl
CuCl
2
–
–
92
83
82
76
53
76
79
–
71
24
85
89
81
67
84
87
76
91
(S)
(S)
(S)
(S)
(S)
(S)
(S)
–
(S)
(S)
(S)
(S)
(S)
(S)
(S)
(S)
(S)
(S)
[15]
literature data. [d] 30 °C.
1
0
1
1
1
2
1
3
2
1
4
1
5
1
6
2
1
7
1
8
Scheme 6. Formation of copper complex from 18f with CuCl.
1
9
2
0
2
1
Table 4. Screening of reaction conditions for the conjugate addition
of cyclohexanone to β-nitrostyrene.[
a]
2
2
18
39
68
43
[
d]
2
3
Cl
OH
acetone
CHCl /acetone
2
[d]
2
4
15
15
15
2
5
26
3
63
[
a] Yield of isolated product. [b] Determined by HPLC analysis by
employing a Chiralpak AD column. [c] Absolute configuration was
assigned by comparison of the sign of the optical rotation with
literature data. [d] The solvent was dried before use.
[
15]
Entry Solvent
Additive
Yield
[
dr
ee
[%]
%][
b]
[syn/anti]
[c]
[d]
conditions. The results are summarized in Table 4. Initially,
solvents were tested with benzoic acid as the additive
1
2
3
4
5
6
7
8
9
1
1
1
CH
toluene
DMF
3
CN PhCOOH
88
94
66
94
90
40
n.r.
n.r.
76
64
85
90
85:15
88:12
84:16
90:10
85:15
85:15
–
82
85
80
85
85
68
–
PhCOOH
PhCOOH
PhCOOH
PhCOOH
PhCOOH
(Table 4, Entries 1–6). Solvents had an important impact on
[
e]
CHCl
CH Cl
3
the results. Clearly, chloroform was the optimal solvent,
and it gave the desired product in 94% yield with 85% ee.
Subsequently, the influence of additives was studied. No
product was observed in the presence of CF CO H or p-
2
2
DMSO
CHCl3
CHCl
CHCl
CHCl
CHCl
CHCl
CF COOH
3
3
3
3
3
3
PTSA
–
–
3
2
CH
3
COOH
85:15
86:14
83:17
89:11
84
82
79
83
toluenesulfonic acid (PTSA; Table 4, Entries 7 and 8).
0
1
2
p-NBA
PhCOOH
PhCOOH
Rather low yields were achieved with CH CO H and p-ni-
[f]
3
2
trobenzoic acid (p-NBA) as additives (Table 4, Entries 9
and 10). Therefore, benzoic acid was essential to the excel-
lent performance of this catalytic system. The catalyst load-
ing also was examined (Table 4, Entry 11). Reducing the r.t., 48 h. [b] Yield of isolated product. n.r.: no reaction. [c] Deter-
amount of L1 from 10 to 5 mol-% led to a decrease in the mined by H NMR spectroscopy. [d] Determined by HPLC analy-
[g]
[
(
a] Reaction conditions: cyclohexanone (1 mmol), β-nitrostyrene
0.2 mmol), L1 (10 mol-%), additive (10 mol-%), solvent (0.2 mL),
1
sis. [e] Reaction time: 24 h. [f] L1 (5 mol-%). [g] L6 (10 mol-%).
yield. In addition, L6 was tested, and diastereoselectivity
(
(
89:11 dr) and enantioselectivity (83% ee) were observed
Table 4, Entry 12).
Table 5. By using cyclohexanone as a carbonyl substrate, a
With the optimized reaction conditions in hand, we next variety of nitroalkenes were investigated (Table 5, Entries 1–
probed the substrate scope. The results are summarized in 9). Excellent diastereoselectivities (up to 98:2 dr) and
Eur. J. Org. Chem. 2014, 7823–7829
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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7827

Q. Zhang, X. Cui, L. Chen, H. Liu, Y. Wu
SHORT COMMUNICATION
enantioselectivities (86–92% ee) were observed with nitro-
alkenes bearing ortho substituents on the aromatic ring
(Table 5, Entries 2–5). Nitroalkenes bearing 2-chloro- and
2-bromo-substituted aromatic groups displayed excellent re-
activity (up to 93% yield) and enantioselectivity (up to 86%
ee). Though lower yields were obtained for the nitroalkene
bearing a bulky substituent on the aromatic ring, the dia-
stereoselectivity and enantioselectivity reached 97:3 dr and
9
2% ee, respectively (Table 5, Entry 4). A 3-substituted aro-
matic nitroalkene gave better results (94% yield, 84:16 dr,
0% ee; Table 5, Entry 6) than a nitroalkene possessing an
Figure 4. Proposed enamine transition state.
8
yields with up to 92%ee. Ferrocenophane-based amine L1
as an organocatalyst was also successfully used to catalyze
the asymmetric Michael addition of ketones with a variety
of nitro olefins. Moderate to excellent diastereoselectivities
and enantioselectivities were obtained.
aromatic ring bearing a para substituent (55% yield, 89:11
dr, 78% ee; Table 5, Entry 8). The 2-furyl-substituted nitro-
alkene also worked well, and it afforded satisfactory dia-
stereoselectivity (73:27 dr) and a high ee value (88%;
Table 5, Entry 9). Cyclopentanone gave satisfactory results
in terms of diastereoselectivity (74:26 dr) and enantio-
selectivity (75% ee; Table 5, Entry 10). In addition, acetone
was also tested: 45% yield and 29% ee were obtained Experimental Section
Table 5, Entry 11). The absolute configurations of the
products were determined by comparing the HPLC reten-
(
1
General: All chemicals were commercially available. H NMR and
1
3
C NMR spectra were recorded at 400 and 100 MHz, respectively,
with a Bruker DPX400 spectrometer in CDCl . Tetramethylsilane
[
16]
tion times of the products with the literature data.
The
3
stereochemical outcome might be explained by a synclinal
transition state, as depicted in Figure 4, in which the en-
was used as an internal standard. IR spectra were recorded with a
Bruker Vector 22 spectrometer. Optical rotations were measured by
amine attacks the nitroalkene, which leads to the formation using a Perkin–Elmer 341 polarimeter at 20 °C. Mass spectra (EI)
of the major stereoisomer.[
16b]
were performed with an Agilent 6300 series XCT6320 instrument.
Column chromatography was performed with Qingdao Marine
Chemical Factory silica gel (230–400 mesh), and solvents were dis-
tilled before use. X-ray crystallographic data were obtained with a
Rigaku R-Axis-IV X-ray diffractometer.
Table 5. Asymmetric Michael addition reaction of ketones and ni-
[
a]
troalkenes.
Typical Procedure for the Asymmetric Oxidative Coupling Reaction
of 2-Naphthol Derivatives: Ligand (0.014 mmol), CuCl
(
0.014 mmol), and CH
solution was stirred at room temperature for 2 h. The 2-naphthol
derivative (0.14 mmol) and CH CN (1 mL) were added to the re-
3
CN (1 mL) were added to a test tube. The
Entry
R1
(CH
(CH
(CH
(CH
(CH
(CH
(CH
(CH
(CH
(CH
R2 Aryl
Yield
[
dr
ee
[%]
3
%][
b]
(syn/anti)
[c]
[d]
sulting solution. Then, the tube was placed in a bath at the reaction
temperature. After 4 d, the mixture was directly purified by column
chromatography (petroleum ether/ethyl acetate, 3:1) to afford the
corresponding product.
1[e]
2
2
2
2
2
2
2
2
2
2
)
)
)
)
)
)
)
)
)
)
3
3
3
3
3
3
3
3
3
Ph
2-ClC H
6 4
94
93
93
61
72
94
89
55
96
81
45
90:10
89:11
90:10
97:3
85
86
85
92
87
80
85
78
88
75
29
2
3
4
5
6
7
8
9
2-BrC
2-CH
2-F CC
3-CH
4-BrC
4-CH
2-furyl
Ph
Ph
6 4
H
3
OC
6
H
H
H
4
4
4
Typical Procedure for the Asymmetric Michael Addition Reaction:
A mixture of L1 (0.02 mmol), organic acid (0.02 mmol), and chlo-
roform (0.2 mL) was stirred at room temperature for 20 min. The
ketone (1 mmol) was added, and the mixture was stirred for an-
other 10 min. Then, the nitroalkene (0.2 mmol) was added. After
stirring for the stated time, the mixture was quenched with satu-
3
6
H
4
98:2
3
OC
6
84:16
87:13
89:11
73:27
74:26
–
6 4
H
3
OC
6
10
1
2
H
1
H
rated aqueous NH
4
Cl solution, extracted with EtOAc, and dried
with Na SO . The crude product was purified by flash silica gel
chromatography.
2
4
[
a] Reaction conditions: ketone (1 mmol), nitroalkene (0.2 mmol),
L1 (10 mol-%), additive (10 mol-%), solvent (0.2 mL), r.t., 48 h.
b] Yield of isolated product. [c] Determined by 1H NMR spec-
[
Supporting Information (see footnote on the first page of this arti-
cle): Experimental details for the syntheses of the chiral ferroceno-
phanes and the products of the catalytic asymmetric reactions and
troscopy. [d] Determined by HPLC analysis. [e] Reaction time: 24 h.
1
13
H NMR and C NMR spectra and HPLC traces.
Conclusions
Acknowledgments
A series of chiral diamines, including N-substituted 2-
aza-[3]-ferrocenophanes, were successfully prepared and
evaluated in the Cu -catalyzed asymmetric oxidative cou-
We are grateful to the National Natural Science Foundation of
China (20972139, 21102133) and the National Natural Science
I
pling of 2-naphthol derivatives. N-Substituted 2-aza-[3]- Foundation of Henan (082300423201) for financial support of this
ferrocenophane L1 afforded binaphthol derivatives in good research.
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Eur. J. Org. Chem. 2014, 7823–7829

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Received: July 23, 2014
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Published Online: October 30, 2014
Eur. J. Org. Chem. 2014, 7823–7829
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