Chiral phosphine oxide aziridinyl phosphonate as a Lewis base catalyst for enantioselective allylsilane addition to aldehydes

Article abstract of DOI:10.1016/j.tetasy.2015.07.002

A series of chiral Lewis bases, phosphine oxide ferrocenyl aziridinyl methanol 1-4, phosphinyl aziridinyl phosphonates 5 and 6, and phosphine oxide aziridinyl phosphonates 7 and 8 were screened for allylsilane additions to aldehydes. Among the Lewis bases

Full text of DOI:10.1016/j.tetasy.2015.07.002

Tetrahedron: Asymmetry xxx (2015) xxx–xxx
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Tetrahedron: Asymmetry
journal homepage: www.elsevier.com/locate/tetasy
Chiral phosphine oxide aziridinyl phosphonate as a Lewis base
catalyst for enantioselective allylsilane addition to aldehydes
b
b
Özdemir Dogan a, , Adnan Bulut , M. Ali Tecimer
⇑
a Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey
b Department of Chemistry, Kırıkkale University, 71450 Kırıkkale, Turkey
a r t i c l e i n f o
a b s t r a c t
Article history:
A series of chiral Lewis bases, phosphine oxide ferrocenyl aziridinyl methanol 1–4, phosphinyl aziridinyl
phosphonates 5 and 6, and phosphine oxide aziridinyl phosphonates 7 and 8 were screened for allylsilane
additions to aldehydes. Among the Lewis bases, 8 was found to catalyze the reaction by forming the
product in up to 94% yield and with 77% ee.
Received 6 July 2015
Accepted 9 July 2015
Available online xxxx
Ó 2015 Elsevier Ltd. All rights reserved.
Dedicated to the memory of Professor Dr
Tugmac Sayrac
1. Introduction
have recently reported the use of phosphine oxide ferrocenyl azir-
idinyl methanols 1–4 as chiral ligands for the metal catalyzed
Chiral Lewis base catalyzed asymmetric synthesis has gained
much attention and become a popular strategy for the enantiose-
lective synthesis of organic compounds. Silicon has found many
applications in organocatalytic reactions.1 Tetra-coordinated
silicon compounds and chiral Lewis bases can form five- or six-
coordinated hypervalent silicon species in situ and promote
catalytic enantioselective reactions in good yields and enantiose-
lectivities.2 Phosphoramides,3 formamides,4 sulfoxides,5 and
pyridine N-oxides6 have been used as Lewis bases with silicon
for the enantioselective synthesis of organic compounds. Chiral
Lewis bases with phosphine oxide bonds are highly nucleophilic
due to the polarization of the P–O bond. As a result, when used
with trichlorosilyl compounds, they are able to form hypervalent
silicates as intermediates to provide high enantioselectivity.7 One
important use of these bases with silicon is the enantioselective
allylsilane addition to aldehydes. This is an important carbon–
carbon bond formation reaction which produces chiral homoallylic
alcohols. Nakajima et al. reported the use of BINAPO as the Lewis
base catalyst for the enantioselective addition of allyltrichlorosi-
lanes to aldehydes.8 Kocovsky et al. reported the bromoallyl-
trichlorosilane addition to aldehydes catalyzed by BINAPO and
other phosphine dioxide Lewis bases.9 Scettri et al. reported chiral
imino- and amino-sulfoxides as activators of allyltrichlorosilane in
the asymmetric allylation of aldehydes.10 Ishimaru et al. used
C2-symmetrical chiral bisformamides for asymmetric allylation
reactions of aromatic aldehydes with allyltrichlorosilane in the
presence of potassium carbonate and potassium phosphate.11 We
enantioselective synthesis of organic compounds12 and phosphine
oxide aziridinyl phosphonates 7 and 8 as chiral Lewis bases for the
Abramov-type phosphonylation of aldehydes.13 Herein we report
the results of these compounds 1–8 as chiral Lewis base catalysts
for the enantioselective allylsilane addition to aldehydes.
2. Results and discussion
The first series of chiral Lewis bases 1–4 were synthesized via a
Gabriel–Cromwell reaction starting from acryloyl ferrocene.12a The
second series of chiral Lewis bases 5–8 were also synthesized by
the same reaction starting from vinyl phosphonate or its
a-
tosylated derivative Figure 1.13 After preparing the chiral Lewis
bases, their performance was tested for the allylsilane addition
reaction to aldehydes and the results are summarized in Table 1.
As can be seen from these results, the first series of Lewis bases
showed no enantioselectivity (entries 1–7). Therefore Lewis base
screening studies were continued with the second series 5–8. In
this series, the results were not satisfactory for Lewis bases 5–7;
the products were isolated in low yields and with poor enantiose-
lectivities (entries 8–15). Fortunately, Lewis base 8 showed a
promising result in the first trial (entry 16) therefore further
optimization was continued with this Lewis base. Repeating the
reactions with this Lewis base at different temperatures, concen-
trations, solvents, and with different additives, the highest yield
and ee obtained were 55% and 61%, respectively, (entries 17–27).
After obtaining the product in reasonable yield and enantiose-
lectivity, the catalytic effect of Lewis base 8 on different aldehydes
was studied, and the results are summarized in Table 2. The effect
of the electron withdrawing nitro group was very small on the ee,
⇑
Corresponding author. Tel.: +90 312 210 5134.
E-mail address: dogano@metu.edu.tr (Ö. Dogan).
http://dx.doi.org/10.1016/j.tetasy.2015.07.002
0957-4166/Ó 2015 Elsevier Ltd. All rights reserved.
Please cite this article in press as: Dogan, Ö;. et al. Tetrahedron: Asymmetry (2015), http://dx.doi.org/10.1016/j.tetasy.2015.07.002

2
Ö. Dogan et al. / Tetrahedron: Asymmetry xxx (2015) xxx–xxx
Ph
P
Ph
P
Ph
P
Ph
P
Et
Et
Et
Et
Ph
Ph
O
Ph
O
Ph
H
OH
H
OH
H
OH
H
O
O
O
N
N
N
N
Fc
Fc
Fc
Fc
H
H
H
H
H
1
2
3
4
Fc = ferrocenyl
Ph
P
Ph
P
Et
Et
Et
Et
Ph
O
Ph
O
H
H
H
PPh2
O
PPh2
N
N
N
N
O
O
O
P
P
P
P
OEt
OEt
OEt
8
OEt
5
6
7
POAP-B
OEt
OEt
OEt
OEt
Figure 1. Structures of Lewis bases.
Table 1
Lewis base screening and optimization studiesa
O
OH
Lewis base
SiCl3
+
H
Entry
Lewis base
Concn (M)
Additive
Solvent
Temp (°C)
Time (h)
Yieldb (%)
eec (%)
Confign.d
1
2
3
4
5
6
7
8
1
2
3
4
3
1
1
5
5
6
6
6
7
7
7
8
8
8
8
8
8
8
8
8
8
8
8
0.40
0.25
0.40
0.40
0.40
0.40
0.40
0.30
0.30
0.30
0.30
0.30
0.40
0.15
0.15
0.40
0.40
0.40
0.40
0.40
0.50
0.50
0.50
0.50
0.50
0.50
0.50
—
—
—
—
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
DCM
CH3CN
DCM
CH3CN
CH3CN
DCM
CH3CN
DCM
DCM
CH3CN
CH3CN
CH3CN
Toluene
CH3CN
CH3CN
DCM
0
0
0
0
0
0
0
0
0
48
48
48
24
48
48
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
48
24
24
24
nd
nd
nd
83
9
nd
nd
nd
rac
nd
rac
nd
17
12
15
5
Bu4NI
Bu4NI
DMF
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
—
70
nd
34
34
34
34
34
72
25
42
45
22
78
23
25
40
45
45
nd
34
56
58
(S)
(S)
(R)
(R)
(R)
(S)
(R)
(R)
(R)
(R)
(R)
(S)
(R)
(S)
(S)
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26e
27e
0
À20
À20
0
5
10
10
10
35
10
33
17
7
27
45
rac
nd
58
61
21
À78
Rt
Rt
À78
Rt
Rt
Rt
Rt
Rt
Rt
Rt
Rt
Rt
Rt
—
Bu4NI
Et3N
Et3N
DABCO
TMEDA
DIPEA
DIPEA
DIPEA
DCM
DCM
DCM
DCM
(S)
(S)
(S)
DCM
a
Conditions: benzaldehyde (0.30 mmol), allyltrichlorosilane (0.36 mmol), Lewis base (0.03 mmol), and additive (0.30 mmol). Reaction was stirred at room temperature for
24 h.
b
Isolated yields.
Determined by chiral HPLC.
c
d
e
The absolute configurations were assigned by comparison of the chiral HPLC data reported in the literature.3d
DIPEA was used in 0.5 equiv.
but significantly changed the yield depending on the position on
the aromatic ring (entries 2–4). While the electron donating
methyl group at the ortho-position of the aldehyde formed the pro-
duct in highest yield and with acceptable ee (entry 5), electron
donors at the para-position of the aldehyde formed the products
in acceptable yield but with low enantioselectivities (entries 7
and 8). The highest ee was obtained with m-bromobenzaldehyde
(entry 6). For the naphthaldehydes, the yield and ee were good
for 2-naphthaldehyde but the ee was relatively low for 1-naph-
thaldeyde (entries 9 and 10). This result may be attributed to the
steric effects.
3. Conclusion
A series of chiral Lewis bases were screened for catalytic
enantioselective allylsilane additions to aromatic aldehydes.
Lewis bases with a phosphine oxide group and a ferrocenyl sub-
stituent on the aziridine ring 1–4 did not show catalytic activity
for this reaction. Lewis bases 5 and 6 with a phosphinyl group
and a phosphonate unit on their structure showed small catalytic
activity. Lewis bases 7 and 8 with a phosphine oxide and phospho-
nate units in their structures showed acceptable catalytic activity.
Aldehyde screening studies with the most active Lewis base 8
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Ö. Dogan et al. / Tetrahedron: Asymmetry xxx (2015) xxx–xxx
3
ee (R); 1H NMR d 7.31–7.19 (m, 5H), 5.83–5.75 (m, 1H), 5.16–
5.03 (m, 2H), 4.70–4.65 (m, 1H), 2.51–2.39 (m, 2H), 1.95 (d,
J = 2.9 Hz, 1H); 13C NMR d 41.4, 71.3, 116.1, 123.4, 125.1, 126.4,
132.1; HPLC: Chiralcel OD column, UV detection at 220 nm,
eluent: hexane/2-propanol 95:5, flow 1.0 mL minÀ1, tR = 21.7 min
(R, minor), 28.5 min (S, major).
Table 2
Aldehyde screening studiesa
OH
O
POAP-B 8 (10 mol%)
+
SiCl3
R
*
R
H
DIPEA (1 equiv.)
DCM, rt
9a-j
10a-j
Entry
R
Substrate
Yieldb (%)
eec (%)
Confign.d
4.2.2. (S)-1-(4-Nitrophenyl)-3-buten-1-ol 10b
Rf = 0.12 hexane/ethyl acetate 10:1; [
a
]
25 = À30.9 (c 3.3, CH2Cl2)
1
2
3
4
5
6
7
8
9
10
Ph
9a
9b
9c
9d
9e
9f
9g
9h
9i
56
60
21
73
94
73
62
61
81
67
61
60
57
61
61
77
24
32
67
18
(S)
(S)
(S)
(S)
(S)
(S)
(S)
(S)
(S)
(R)
D
for 60% ee (S). Lit.3d
[
a]
27 = +31.7 (c 3.5, benzene) for 21% ee (R); 1H
p-NO2C6H4
m-NO2C6H4
o-NO2C6H4
o-MeC6H4
m-BrC6H4
p-MeOC6H4
p-MeC6H4
2-Naphthyl
1-Naphthyl
D
NMR d 8.21 (d, J = 8.8 Hz, 2H), 7.54 (d, J = 8.6 Hz, 2H), 5.91–5.63 (m,
1H), 5.27–5.12 (m, 2H), 4.87 (dd, J = 7.8, 4.7 Hz, 1H), 2.69–2.52 (m,
1H), 2.50–2.44 (m, 1H), 2.24 (br s, 1H); 13C NMR d 43.8, 72.2, 96.1,
119.9, 123.8, 126.7, 133.0, 151.1; HPLC: Chiralcel AS-H column, UV
detection at 210 nm, eluent: hexane/2-propanol 98:2, flow
0.7 mL minÀ1, tR = 81.4 min (R, minor), 88.7 min (S, major).
9j
a
Conditions: arylaldehyde (0.30 mmol), allyltrichlorosilane (0.36 mmol),
8
4.2.3. (S)-1-(3-Nitrophenyl)-3-buten-1-ol 10c
i
(0.03 mmol), Pr2NEt (0.30 mmol), and DCM (0.6 mL). Reaction was stirred at room
temperature for 24 h.
Rf = 0.12 hexane/ethyl acetate 10:1; [
a]
25 = À19.8 (c 0.4, CH2Cl2)
D
for 57% ee (S). Lit.6f
[a
]
D
25 = +47 (c 1.0, CHCl3) for 72% ee (R); 1H NMR
b
Isolated yields.
Determined by chiral HPLC.
The absolute configurations were assigned by comparison of the sign of the
c
d 8.15 (s, 1H), 8.05 (m, 1H), 7.61 (d, J = 7.7 Hz, 1H), 7.44
d
(t, J = 7.9 Hz, 1H), 5.72 (m, 1H), 5.12 (m, 2H), 4.77 (dd, J = 8.1, 4.6
1H), 2.50 (m, 1H), 2.40 (m, 1H), 2.17 (br s, 1H); 13C NMR d 42.9,
71.1, 118.7, 119.9, 121.5, 128.3, 130.9, 132.2, 144.9; HPLC:
Chiralcel OD column, UV detection at 220 nm, eluent: hexane/
specific rotations with the ones reported in the literature. For compound 10d,
assignment was based on the chiral HPLC data.5f
2-propanol 150:1, flow 1 mL minÀ1
, tR = 62.3 min (R, minor),
formed homoallylic alcohols in reasonable yields and enantioselec-
tivities. These results warrant further development of phosphine
oxide aziridinyl phosphonates as organocatalysts for catalytic
asymmetric transformations.
69.4 min (S, major).
4.2.4. (S)-1-(2-Nitrophenyl)-3-buten-1-ol 10d
Rf = 0.21 hexane/ethyl acetate 10:1; 1H NMR d 8.15 (s, 1H), 8.05
(m, 1H), 7.61 (d, J = 7.7 Hz, 1H), 7.44 (t, J = 7.9 Hz, 1H), 5.72 (m, 1H),
5.14–5.09 (m, 2H), 4.77 (dd, J = 8.1, 4.6 Hz, 1H), 2.54–2.47 (m, 1H),
2.43–2.36 (m, 1H), 2.17 (br s, 1H); 13C NMR d 42.9, 68.5, 118.6,
124.4, 128.2, 133.3, 134.0, 139.3, 147.8; HPLC: Chiralcel OD col-
umn, UV detection at 210 nm, eluent: hexane/2-propanol 99:1,
flow 0.5 mL minÀ1, tR = 50.2 min (R, minor), 66.2 min (S major)
for 61% ee. Lit.5f HPLC: Chiralcel OD column, eluent: hexane/
4. Experimental
4.1. General
All asymmetric reactions were performed under an inert atmo-
sphere in dry glassware. DCM was dried and distilled from calcium
hydride prior to use. Diisopropylethylamine was distilled from cal-
cium hydride. Products were purified by flash column chromatog-
raphy on Silica Gel 60 (Merck, 230–400 mesh ASTM). TLC analyses
2-propanol 99:1, flow 0.5 mL minÀ1
, tR = 72.5 min (R minor),
77.7 min (S major).
were performed on 250 lm Silica Gel 60 F254 plates. Enantiomeric
excess (ee) was determined by chiral HPLC. IR spectra are reported
in reciprocal centimeters (cmÀ1). 1H and 13C NMR spectra were
reported on a Brucker spectrospin Avance DPX-400 Ultra shield
instrument at 400 MHz and 100 MHz respectively relative to
TMS. A Rudolph Research Analytical Autopol III Polarimeter was
used to measure optical rotations.
4.2.5. (S)-1-(2-Methylphenyl)-3-buten-1-ol 10e
Rf = 0.32 hexane/ethyl acetate 10:1; [
a
]
D
25 = À44.3 (c 1.2, CH2Cl2)
for 61% ee (S). Lit.14a
[
a]
24 = +68.8 (c 1.1, benzene) for 93% ee (R); 1H
D
NMR d 7.41 (d, J = 7.7 Hz, 1H), 7.21–7.00 (m, 3H), 5.86–5.74 (m,
1H), 5.11 (dd, J = 20.7, 5.2 Hz, 2H), 4.90 (dd, J = 7.6, 3.1 Hz, 1H),
2.50–2.30 (m, 2H), 2.26 (s, 3H), 1.85 (br s, 1H); 13C NMR d 19.1,
42.6, 69.8, 125.1, 126.2, 127.3, 130.4, 134.4, 134.8; HPLC:
Chiralcel AD-H column, UV detection at 210 nm, eluent:
4.2. General procedure for asymmetric allyl trichlorosilane
additions to aldehydes
hexane/2-propanol 90:10, flow 1 mL minÀ1
, tR = 7.1 min (R,
minor), 8.1 min (S major).
Chiral Lewis base 8 (13 mg, 0.03 mmol), dry DCM (0.6 mL),
i
benzaldehyde (30
allyltrichlorosilane (51
l
L, 0.30 mmol), Pr2NEt (52
l
L, 0.30 mmol), and
4.2.6. (S)-1-(3-Bromophenyl)-3-buten-1-ol 10f
l
L, 0.36 mmol) were added respectively to
Rf = 0.30 hexane/ethyl acetate 10:1; [
a
]
25 = À41.6 (c 1.3, CH2Cl2)
D
a dried Schlenk tube under a nitrogen atmosphere. The resulting
mixture was then stirred at room temperature for 24 h, after which
the reaction mixture was hydrolyzed by adding saturated NaHCO3
(5 mL), then extracted with EtOAc (3 Â 5 mL). The combined organic
phase was dried over MgSO4. The concentrated crude product was
purified by flash column chromatography using silica gel
(hexane/acetone 2:1) to give homoallylic alcohol in 56% yield
(25 mg, 0.17 mmol). Enantioselectivity was determined by chiral
HPLC.
for 77% ee (S). Lit.14b
[a]
20 = À39.5 (c 0.6, CHCl3) for 90% ee (S); 1H
D
NMR d 7.53 (s, 1H), 7.42–7.39 (m, 1H), 7.27–7.22 (m, 2H), 5.82–
5.78 (m, 1H), 5.21–5.17 (m, 2H), 4.72 (dd, J = 7.9, 4.8 Hz, 1H),
2.52–2.48 (m, 2H), 2.17 (br s, 1H); 13C NMR d 43.8, 72.5, 96.1,
119.0, 122.7, 124.4, 128.9, 130.6, 133.9, 146.1; HPLC: Chiralcel
OD column, UV detection at 210 nm, eluent: hexane/2-propanol
150:1, flow 1 mL minÀ1
, tR = 35.4 min (S, major), 43.2 min
(R minor).
4.2.7. (S)-1-(4-Methoxyylphenyl)-3-buten-1-ol 10g
4.2.1. (S)-1-Phenyl-3-buten-1-ol 10a
Rf = 0.18 hexane/ethyl acetate 10:1; [
a
]
25 = À6.8 (c 1.1, CH2Cl2)
D
Rf = 0.12, hexane/ethyl acetate 10:1;
[
a]
25 = À17.1 (c 0.2,
for 24% ee (S). Lit.3d
[
a]
27 = +20.0 (c 4.0, benzene) for 21% ee (R);
D
D
CH2Cl2) for 61% ee (S). Lit.3d
[a]
26 = +31.7 (c 3.5, benzene) for 61%
1H NMR d 7.21 (d, J = 8.6 Hz, 2H), 6.81 (d, J = 8.7 Hz, 2H), 5.82–
D
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4
Ö. Dogan et al. / Tetrahedron: Asymmetry xxx (2015) xxx–xxx
5.61 (m, 1H), 5.15–4.98 (m, 2H), 4.61 (t, J = 6.5 Hz, 1H), 3.73 (s, 3H),
2.42 (t, J = 6.9 Hz, 2H), 1.91 (br s, 1H); 13C NMR d 43.8, 55.3, 73.0,
96.1, 113.8, 118.2, 127.1, 134.6; HPLC: Chiralcel OD column, UV
detection at 210 nm, eluent: hexane/2-propanol 98:2, flow
1 mL minÀ1, tR = 19.9 min (R, minor), 24.5 min (S major).
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25 = +5.0 (c 0.3, CH2Cl2)
D
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Kotani, S.; Ito, M.; Nozaki, H.; Sugiura, M.; Masamichi Ogasawara, M.;
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Sugiura, M.; Nakajima, M. Tetrahedron Lett. 2011, 52, 2834–2836.
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1173–1175.
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for 32% ee (S). Lit.5e
[a
]
D
25 = À31.5 (c 1.0, CHCl3) for 79% ee (S); 1H
NMR d 7.17 (d, J = 6.8 Hz, 2H), 7.09 (d, J = 7.9 Hz, 2H), 5.80–5.65
(m, 1H), 5.15–5.02 (m, 2H), 4.68–4.60 (m, 1H), 2.50–2.39 (m,
2H), 2.25 (s, 3H), 1.90 (br s, 1H); 13C NMR d 21.2, 43.6, 73.2,
118.1, 125.7, 129.2, 134.5, 137.3, 140.3; HPLC: Chiralcel AD
column, UV detection at 210 nm, eluent: hexane/2-propanol
98:2, flow 1 mL minÀ1, tR = 15.6 min (R, minor), 17.3 min (S major).
4.2.9. (S)-1-(2-Naphthyl)-3-buten-1-ol 10i
Rf = 0.33 hexane/ethyl acetate 10:1;
[
a]
25 = À23.6 (c 1.03,
D
CH2Cl2) for 67% ee (R). Lit.6f
[a
]
D
25 = +58.0 (c 1.0, CHCl3) for 83% ee
(R); 1H NMR d 7.73 (m, 4H), 7.45–7.32 (m, 3H), 5.76–5.72 (m,
1H), 5.16–5.00 (m, 2H), 4.80 (dd, J = 7.1, 5.7 Hz, 1H), 2.62–2.41
(m, 2H), 2.20 (br s, 1H); 13C NMR d 42.7, 72.4, 117.5, 123.0,
123.5, 124.8, 125.1, 126.6, 126.9, 127.2, 131.9, 132.2, 133.3,
140.2; HPLC: Chiralcel OD-H column, UV detection at 210 nm,
eluent: hexane/2-propanol 95:5, flow 0.7 mL minÀ1, tR = 35.5 min
(R, major), 38.9 min (S minor).
4.2.10. (R)-1-(1-Naphthyl)-3-buten-1-ol 10j
Rf = 0.27 hexane/ethyl acetate 10:1; [
a]
25 = +7.1 (c 1.1, CH2Cl2)
D
for 18% ee (R); Lit.6f 27 = +84 (c 1.0, CHCl3) for 84% ee (R); 1H
[a]
D
NMR d 8.08 (d, J = 8.1 Hz, 1H), 7.88 (d, J = 7.3 Hz, 1H), 7.78 (d,
J = 8.1 Hz, 1H), 7.67 (d, J = 6.9 Hz, 1H), 7.55–7.42 (m, 3H), 5.93
(m, 1H), 5.53 (d, J = 4.7 Hz, 1H), 5.28–5.10 (m, 2H), 2.77 (m, 1H),
2.68–2.53 (m, 1H), 2.17 (br s, 1H); 13C NMR d 42.9, 70.0, 118.4,
122.9, 123.0, 125.4, 125.5, 126.1, 128.0, 129.0, 133.8, 134.8,
139.4; HPLC: Chiralcel OD-H column, UV detection at 210 nm,
eluent: hexane/2-propanol 95:5, flow 0.5 mL minÀ1, tR = 33.9 min
(S minor), 37.5 min (R, major).
11. Tanimura, Y.; Ishimaru, K. Tetrahedron: Asymmetry 2012, 23, 345–349.
12. (a) Eröksüz, S.; Dogan, O.; Garner, P. P. Tetrahedron: Asymmetry 2010, 21, 2535–
2541; (b) Dogan, O.; Bulut, A.; Polat, S.; Tecimer, M. A. Tetrahedron: Asymmetry
2011, 22, 1601–1604; (c) Dogan, O.; Çaglı, E. Turk. J. Chem. 2015, 39, 290–296.
13. Dogan, O.; Isci, M.; Aygun, M. Tetrahedron: Asymmetry 2013, 24, 562–567.
14. (a) Jain, P.; Antilla, J. C. J. Am. Chem. Soc. 2010, 132, 11884–11886; (b) Wang, T.;
Hao, X.-Q.; Huang, J.-J.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. J. Org. Chem. 2013, 78,
8712–8721.
Acknowledgments
We thank the Scientific and Technical Research Council of
Turkey (TUBITAK, Grant No. TBAG-110T073) and the Middle East
Technical University Research Foundation for the financial support.
Please cite this article in press as: Dogan, Ö;. et al. Tetrahedron: Asymmetry (2015), http://dx.doi.org/10.1016/j.tetasy.2015.07.002