An efficient method for the synthesis of α-hydroxyalkyl aryl ketones

Article abstract of DOI:10.1055/s-0028-1083149

Exposure of alkyl aryl ketones to Oxone/trifluoroacetic anhydride in the presence of a catalytic amount of iodobenzene affords α-hydroxyalkyl aryl ketones in good yield. This method provides an effective and economical entry for the installation of α-hydroxy moieties into ketones and should find wide application in the construction of the α-hydroxy ketone subunit in natural product synthesis.

Full text of DOI:10.1055/s-0028-1083149

PAPER
3205
An Efficient Method for the Synthesis of a-Hydroxyalkyl Aryl Ketones
E
C
fficient
S
ynthes
h
is of
a
-Hydr
o
e
xyalkyl
A
r
n
yl
K
etones gqun Chen, Xinghua Feng, Guozhen Zhang, Qin Zhao, Guosheng Huang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax +86(931)8912582; E-mail: hgs2368@163.com
Received 8 May 2008; revised 5 June 2008
O
®
O
Abstract: Exposure of alkyl aryl ketones to Oxone /trifluoroacetic
®
Oxone , TFAA, PhI
R
R
anhydride in the presence of a catalytic amount of iodobenzene af-
fords a-hydroxyalkyl aryl ketones in good yield. This method pro-
vides an effective and economical entry for the installation of a-
hydroxy moieties into ketones and should find wide application in
the construction of the a-hydroxy ketone subunit in natural product
synthesis.
Ar
Ar
H O–MeCN, 90 °C, 15 h
2
OH
Scheme 1
30% aqueous hydrogen peroxide was used to replace part
of the Oxone , no reaction was observed, which showed
that Oxone was not only used as an oxidant but also as a
®
Key words: Oxone®, hydroxylation, iodobenzene, a-hydroxy
®
ketones
strong acid to induce the enolization of acetophenone
(
Table 1, entry 7). As water is a stronger nucleophile than
trifluoroacetic acid, a-trifluoroacetoxy ketones would not
The a-hydroxy carbonyl moiety is a versatile intermediate
be obtained.9
b,14
in the synthesis of many natural products and pharmaceu-
1
ticals. a-Hydroxy ketones can be prepared in various
The effect of temperature on the reaction was studied. As
shown in Table 1, raising the temperature to 100 °C re-
sulted in a decrease in the yield to 52% (entry 3). Increas-
ing the reaction time to 24 hours did not result in a higher
yield (Table 1, entry 4). In this catalytic cycle, iodoarene
would be oxidized to the iodine(III) species which reacts
ways, for example, by the oxidation of preformed enolates
and enolate derivatives using various methods including
2
3
4
organic peracids, singlet oxygen, osmium tetroxide,
5
6
lead(IV) salts, and ozonolysis, by the reduction of dike-
tones, and by the oxidation of epoxides and aziridines.
7
8
There has also been considerable interest in the develop-
ment of direct methods for the synthesis of a-hydroxy ke-
tones using nontoxic hypervalent iodine reagents;9
however, stoichiometric amounts of hypervalent iodine
reagents are required and equimolecular amounts of iodo-
benzene are produced as waste in the reaction. To over-
come this drawback, Ochiai and co-workers have
developed a method for the a-acetoxylation of ketones us-
with the alkyl aryl ketones to give the a-hydroxyalkyl aryl
ketones and iodoarene.1
0,15
When acetic anhydride was
used instead of trifluoroacetic anhydride, there was a de-
crease in the yield; this showed that the electron-with-
drawing ligand increases the oxidative efficiency of
hypervalent iodine reagents (Table 1, entries 2 and 5). If
there was no ligand, there was an obvious decrease in the
yield (15%) of 2-hydroxyacetophenone (Table 1, entry 6).
1
0
ing only a catalytic amount of iodobenzene. Such a cat-
alytic cycle has not previously been realized, except for
Table 1 Oxidation of Acetophenone under Various Conditionsa
1
1
®
electrochemical oxidants. Oxone , a potassium triple
salt containing potassium peroxymonosulfate, is an effec-
b
Entry
Temp (°C)
Conversion (%)
Yield (%)
1
2
®
tive oxidant for numerous transformations. Oxone has
also been demonstrated to oxidize iodoarenes to the hy-
1
2
70
90
100
90
90
90
90
70
88
73
84
89
30
–
46
74
52
74
67
15
1
3
®
pervalent iodine species. The use of Oxone as an effi-
cient and mild oxidant has grown rapidly. This is due in
part to the stability, ease of transport, nontoxic nature,
nonpolluting byproducts, and cost-effectiveness of
3
4c
®
Oxone .
5d
6e
In this paper we present the synthesis of a-hydroxyalkyl
®
aryl ketones from alkyl aryl ketones in which Oxone
serves as a terminal oxidant (Scheme 1). Exposure of
7f
–
®
acetophenone to Oxone (2.7 equiv)/trifluoroacetic anhy-
a
®
dride (7.0 equiv) in the presence of a catalytic amount of
iodobenzene (20 mol%) at 90 °C for 15 hours afforded 2-
hydroxyacetophenone in 74% yield (Table 1, entry 2). If
Reaction conditions: acetophenone (10 mmol), Oxone (2.7 equiv),
TFAA (7.0 equiv), PhI (0.2 equiv), H O–MeCN (1:3, v/v), 15 h.
2
b
Isolated yields.
Reaction time: 24 h.
c
d
Ac O was used instead of TFAA.
2
e
TFAA was not used.
SYNTHESIS 2008, No. 20, pp 3205–3208
x
x.
x
x
.
2
0
0
8
f
®
Oxone (1.0 equiv) and 30% aq H O (2.7 equiv) were used instead
2
2
Advanced online publication: 25.09.2008
DOI: 10.1055/s-0028-1083149; Art ID: F10108SS
Georg Thieme Verlag Stuttgart · New York
®
of Oxone (2.7 equiv).
©

3
206
C. Chen et al.
PAPER
®
Table 2 a-Hydroxylation of Alkyl Aryl Ketones with Oxone /Tri-
According to the results in Table 2, when the substituent
on the aryl ring in acetophenone was an electron-with-
drawing group, a higher yield was obtained than when it
was an electron-donating group (Table 2, entries 7–9 and
12). The reaction was also found to be influenced by steric
effects; when propiophenone and 1-(naphthalen-1-yl)eth-
anone were converted into a-hydroxy ketones using this
method, the product yield decreased from 74% to 58%
and 56%, respectively (Table 2, entries 2 and 13).
a
fluoroacetic Anhydride
b
Entry
1
Product
Conversion (%) Yield (%)
O
88
80
74
58
OH
Ph
O
2
Ph
OH
In conclusion, the conversion of alkyl aryl ketones into
3
4
91
91
80
82
OH
®
a-hydroxyalkyl aryl ketones using Oxone and trifluoro-
Cl
acetic anhydride as a terminal oxidant has been accom-
plished in good yields. The present approach provides an
effective and economical entry for the installation of
a-hydroxy moieties into ketones and should find wide ap-
plication in the construction of the a-hydroxy ketone sub-
unit in natural product synthesis.
O
O
OH
Br
5
6
7
8
9
OH
93
79
70
86
76
89
70
63
50
62
50
80
I
O
1
OH
NMR spectra were recorded on a Mercury 4N-PEG-300 ( H: 300
1
3
MeO
O2N
Ph
MHz; C: 75 MHz) spectrometer, using CDCl or DMSO-d as a
3 6
O
solvent and TMS as the internal standard. IR spectra were recorded
as KBr pellets or KBr film on a Nicolet Nexus 670 FT IR spectro-
photometer. Mass spectra were recorded using the EI method on a
HP 5998 mass spectrometer. Melting points are uncorrected.
OH
O
OH
2-Hydroxyacetophenone; Typical Procedure
®
O
A soln of Oxone (16.6 g, 27 mmol), TFAA (9.8 mL, 70 mmol), and
H O (50 mL) was stirred at 40 °C for 7 h, and then cooled to r.t.
OH
2
Acetophenone (1.20 g, 10 mmol) and PhI (0.4 g, 2 mmol) in MeCN
(
9
150 mL) were added at r.t. The resulting solution was stirred at
0 °C for 15 h (the progress of the reaction was monitored by TLC).
Then, CH Cl (15 mL) was added. The mixture was neutralized
O
1
1
1
1
0
1
2
3
Br
OH
2
2
with a cooled 10% aq Na CO soln and extracted with CH Cl (3 ×
2
3
2
2
7
0 mL). The combined organic phase was washed with brine (20
O
mL), dried (anhyd MgSO ), filtered, and concentrated. The residue
4
78
73
75
61
52
56
MeO
was purified by column chromatography [silica gel (200–300
mesh), petroleum ether–EtOAc, 8:1] to give 2-hydroxyacetophe-
none; yield: 1.00 g (74%).
OH
O
O N
2
2
-Hydroxyacetophenone
OH
White solid; mp 86–89 °C (n-hexane).
–
1
IR (KBr): 3430, 1683 cm .
O
1
O
H NMR (300 MHz, CDCl ): d = 7.93 (d, J = 7.2 Hz, 2 H), 7.66–
3
OH
7
.26 (m, 3 H), 4.89 (s, 2 H), 3.52 (s, 1 H).
1
3
C NMR (75 MHz, CDCl ): d = 198.4, 134.3, 133.3, 128.9, 127.7.
3
MS (EI): m/z = 136, 105, 77.
1
1
4
5
O
88
81
52
63
Anal. Calcd for C H O : C, 70.57; H, 5.92. Found: C, 70.68; H,
8
8
2
5
.80.
OH
2
-Hydroxypropiophenone
O
Colorless liquid.
–
1
IR (KBr): 3444, 1685 cm .
OH
OH
1
H NMR (300 MHz, CDCl ): d = 7.93 (d, J = 7.8 Hz, 2 H), 7.66–
3
7
.48 (m, 3 H), 5.17 (q, J = 7.2 Hz, 1 H), 3.79 (s, 1 H), 1.45 (d,
16
O
76
48
J = 7.2 Hz, 3 H).
1
3
C NMR (75 MHz, CDCl ): d = 202.3, 133.9, 133.2, 128.8, 128.6,
3
6
9.3, 22.2.
a
®
MS (EI): m/z = 150, 122, 105.
Reaction conditions: ketone (0.3 mmol), Oxone (2.7 equiv), TFAA
(
7.0 equiv), PhI (0.2 equiv), H O–MeCN (1:3, v/v), 90 °C, 15 h.
Isolated yields.
Anal. Calcd for C H O : C, 71.98; H, 6.71. Found: C, 71.88; H,
6.74.
2
9
10
2
b
Synthesis 2008, No. 20, 3205–3208 © Thieme Stuttgart · New York

PAPER
Efficient Synthesis of a-Hydroxyalkyl Aryl Ketones
3207
4
¢-Chloro-2-hydroxyacetophenone
2-Hydroxy-4¢-phenylacetophenone
Pale-yellow solid; mp 125–127 °C (EtOH).
White solid; mp 120–123 °C (EtOH).
–
1
IR (KBr): 3418, 1684 cm–1.
IR (KBr): 3400, 1680 cm .
1
1
H NMR (300 MHz, DMSO-d ): d = 7.92 (d, J = 8.6 Hz, 2 H), 7.57
H NMR (300 MHz, CDCl ): d = 8.00 (d, J = 8.4 Hz, 2 H), 7.73 (d,
6
3
(
d, J = 8.6 Hz, 2 H), 5.14 (t, J = 5.7 Hz, 1 H), 4.75 (d, J = 5.7 Hz,
J = 8.4 Hz, 2 H), 7.63 (q, J = 7.8 Hz, 2 H), 7.50–7.26 (m, 3 H), 4.92
2
H).
(d, J = 8.4 Hz, 2 H), 3.55 (t, J = 4.8 Hz, 1 H).
1
3
13
C NMR (75 MHz, DMSO-d ): d = 198.3, 138.2, 133.3, 129.6,
C NMR (75 MHz, CDCl ): d = 197.9, 147.0, 139.5, 132.0, 129.0,
6
3
1
28.9, 65.4.
128.5, 128.3, 127.6, 127.3, 65.4.
MS (EI): m/z = 172, 170, 142, 139, 113, 111, 75.
MS (EI): m/z = 212, 181, 152.
Anal. Calcd for C H ClO : C, 56.31; H, 4.14. Found: C, 56.23; H,
Anal. Calcd for C H O : C, 79.22; H, 5.70. Found: C, 80.01; H,
8
7
2
14 12
2
3
.84.
5.55.
4
¢-Bromo-2-hydroxyacetophenone
2-Hydroxy-4¢-methylacetophenone
Light-yellow solid; mp 81–83 °C (EtOH).
White solid; mp 118–120 °C (EtOH).
–
1
IR (KBr): 3434, 1682 cm–1.
IR (KBr): 3423, 1657 cm .
1
1
H NMR (300 MHz, DMSO-d ): d = 7.85 (d, J = 8.1 Hz, 2 H), 7.72
H NMR (300 MHz, CDCl ): d = 7.83 (d, J = 8.1 Hz, 2 H), 7.30 (d,
6
3
(
d, J = 8.1 Hz, 2 H), 5.16 (t, J = 5.7 Hz, 1 H), 4.77 (d, J = 5.7 Hz, 2
J = 8.1 Hz, 2 H), 4.86 (s, 2 H), 3.57 (s, 1 H), 2.44 (s, 3 H).
H).
13
C NMR (75 MHz, CDCl ): d = 197.9, 145.4, 130.2, 129.6, 127.8,
3
1
3
C NMR (75MHz, DMSO-d ): d = 198.0, 133.1, 131.3, 129.1,
65.3, 21.8.
6
1
26.9, 64.9.
MS (EI): m/z = 150, 119.
MS (EI): m/z = 216, 214, 185, 183, 157, 155.
Anal. Calcd for C H O : C, 71.98; H, 6.71. Found: C, 71.85; H,
9
10
2
Anal. Calcd for C H BrO : C, 44.68; H, 3.28. Found: C, 45.19; H,
6.56.
8
7
2
3
.14.
3
¢-Bromo-2-hydroxyacetophenone
2
-Hydroxy-4¢-iodoacetophenone
White solid; mp 104–106 °C (EtOH).
IR (KBr): 3426, 1660 cm–1.
White solid; mp 140–142 °C (EtOH).
–
1
IR (KBr): 3421, 1652 cm .
1
H NMR (300 MHz, DMSO-d ): d = 8.05 (s, 1 H), 7.91 (d, J = 7.5
6
1
H NMR (300 MHz, DMSO-d ): d = 7.88 (d, J = 8.4 Hz, 2 H), 7.63
d, J = 8.4 Hz, 2 H), 4.84 (s, 2 H), 3.43 (s, 1 H).
Hz, 1 H), 7.84 (d, J = 7.8 Hz, 1 H), 7.49 (dd, J = 7.5, 7.8 Hz, 1 H),
6
(
5.21 (t, J = 4.8 Hz, 1 H), 4.79 (d, J = 4.8 Hz, 2 H).
1
3
13
C NMR (75 MHz, DMSO-d ): d = 198.8, 137.7, 133.8, 131.1,
C NMR (75 MHz, DMSO-d ): d = 198.3, 136.7, 136.0, 131.1,
6
6
1
29.3, 65.3.
130.2, 126.7, 122.2, 65.5.
MS (EI): m/z = 262, 231, 203.
MS (EI): m/z = 216, 214, 185, 183, 157, 155.
Anal. Calcd for C H BrO : C, 44.68; H, 3.28. Found: C, 45.10; H,
Anal. Calcd for C H IO : C, 36.67; H, 2.69. Found: C, 37.18; H,
8
7
2
8
7
2
2
.52.
3.12.
2
-Hydroxy-4¢-methoxyacetophenone
2-Hydroxy-3¢-methoxyacetophenone
Colorless solid; mp 49–51 °C (EtOH).
Pale-yellow solid; mp 104–107 °C (EtOH).
–
1
IR (KBr): 3428, 1685 cm–1.
IR (KBr): 3424, 1688 cm .
1
1
H NMR (300 MHz, DMSO-d ): d = 7.88 (d, J = 8.7 Hz, 2 H), 7.02
H NMR (300 MHz, CDCl ): d = 7.48–7.37 (m, 3 H), 7.17 (d,
6
3
(
d, J = 8.7 Hz, 2 H), 4.94 (t, J = 6.0 Hz, 1 H), 4.71 (d, J = 6.0 Hz, 2
J = 8.1 Hz, 1 H), 4.91 (s, 2 H), 3.87 (s, 3 H), 3.56 (s, 1 H).
H), 3.82 (s, 3 H).
13
C NMR (75 MHz, CDCl ): d = 198.3, 159.9, 134.5, 129.9, 120.6,
3
1
3
C NMR (75 MHz, DMSO-d ): d = 198.1, 163.9, 130.5, 128.1,
120.1, 111.9, 65.5, 55.4.
6
1
14.7, 65.7, 56.2.
MS (EI): m/z = 166, 135, 107, 92.
MS (EI): m/z = 166, 135, 107, 92.
Anal. Calcd for C H O : C, 65.05; H, 6.07. Found: C, 65.11; H,
9
10
3
Anal. Calcd for C H O : C, 65.05; H, 6.07. Found: C, 65.13; H,
5.91.
9
10
3
5
.98.
2
-Hydroxy-3¢-nitroacetophenone
2
-Hydroxy-4¢-nitroacetophenone
Light-yellow solid; mp 69–70 °C (EtOH).
IR (KBr): 3422, 1656 cm–1.
Yellow solid; mp 138–140 °C (EtOH).
–
1
IR (KBr): 3422, 1658 cm .
1
H NMR (300 MHz, DMSO-d ): d = 8.59 (s, 1 H), 8.43 (d, J = 8.1
6
1
H NMR (300 MHz, DMSO-d ): d = 8.33 (d, J = 8.4 Hz, 2 H), 8.14
d, J = 8.4 Hz, 2 H), 5.31 (t, J = 5.7 Hz, 1 H), 4.84 (d, J = 5.7 Hz, 2
Hz, 1 H), 8.32 (d, J = 7.5 Hz, 1 H), 7.80 (dd, J = 8.1, 7.5 Hz, 1 H),
6
(
5.33 (s, 1 H), 4.85 (s, 2 H).
H).
13
C NMR (75 MHz, DMSO-d ): d = 197.9, 148.0, 135.8, 134.0,
6
1
3
C NMR (75 MHz, DMSO-d ): d = 198.2, 149.5, 138.9, 128.6,
130.6, 127.5, 122.1, 65.8.
6
1
23.4, 65.4.
MS (EI): m/z = 181, 150, 122.
MS (EI): m/z = 181, 150, 122.
Anal. Calcd for C H NO : C, 53.04; H, 3.89. Found: C, 53.06; H,
8
7
4
Anal. Calcd for C H NO : C, 53.04; H, 3.89. Found: C, 53.16; H,
3.79.
8
7
4
3
.74.
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3
208
C. Chen et al.
PAPER
2
-Hydroxy-1-(naphthalen-1-yl)ethanone
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–
1
IR (KBr): 3413, 1648 cm .
(
1
H NMR (300 MHz, CDCl ): d = 8.89 (d, J = 8.7 Hz, 1 H), 8.11–
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3
7
.88 (m, 3 H), 7.70–7.50 (m, 3 H), 4.93 (s, 3 H), 3.74 (s, 1 H).
1
3
C NMR (75 MHz, CDCl ): d = 201.2, 134.5, 133.9, 130.7, 130.3,
3
1
28.7, 128.6, 128.4, 126.8, 125.5, 124.3, 66.6.
(
3
f) Koike, T.; Murata, K.; Ikariya, T. Org. Lett. 2000, 2,
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(
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12
10
2
5
.20.
(
2
-Hydroxy-4¢-methylpropiophenone
1
972, 2423. (b) Friedrich, E.; Lutz, W. Angew. Chem., Int.
Colorless solid; mp 47–49 °C (n-hexane).
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–
1
IR (KBr): 3430, 1680 cm .
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1
H NMR (300 MHz, CDCl ): d = 7.83 (d, J = 8.4 Hz, 2 H), 7.28 (d,
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3
J = 8.4 Hz, 2 H), 5.13 (q, J = 6.6 Hz, 1 H), 3.82 (s, 1 H), 2.43 (s, 3
H), 1.44 (d, J = 6.6 Hz, 3 H).
1
3
1976, 41, 1673.
C NMR (75 MHz, CDCl ): d = 201.9, 145.0, 130.7, 129.5, 128.8,
3
(
6) (a) Clark, R. D.; Heathcock, C. H. Tetrahedron Lett. 1974,
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9.1, 22.4.
2
MS (EI): m/z = 164, 149, 119, 91.
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(
7) Nakamura, K.; Kondo, S.-I.; Kawai, Y.; Hida, K.; Kitano,
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Anal. Calcd for C H O : C, 73.15; H, 7.37. Found: C, 73.21; H,
10
12
2
7
.21.
(
2
-Hydroxyindan-1-one
Colorless solid; mp 79–82 °C (n-hexane).
2
003, 68, 9119. (c) Gravil, S.; Veschambre, H.; Chênevert,
R.; Bolte, J. Tetrahedron Lett. 2006, 47, 6153.
–
1
IR (KBr): 3144, 1719 cm .
1
H NMR (300 MHz, CDCl ): d = 7.77 (d, J = 7.5 Hz, 1 H), 7.66–
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3
7
3
.61 (m, 1 H), 7.47–7.37 (m, 2 H), 4.55 (dd, J = 4.8, 8.1 Hz, 1 H),
.58 (dd, J = 8.1, 16.5 Hz, 1 H), 3.04 (s, 1 H), 3.02 (dd, J = 4.8, 16.5
Hz, 1 H).
1
3
C NMR (75 MHz, CDCl ): d = 206.5, 150.9, 135.8, 133.9, 128.0,
3
1
26.8, 124.4, 74.2, 35.1.
(
10) Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.;
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MS (EI): m/z = 148, 119, 91.
Anal. Calcd for C H O : C, 72.96; H, 5.44. Found: C, 73.01; H,
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9
8
2
5
.21.
4725.
2
-Hydroxy-1-tetralone
(12) (a) Clark, J. H.; Cork, D. G. J. Chem. Soc., Chem. Commun.
1982, 635. (b) Denmark, S. E.; Forbes, D. C.; Hays, D. S.;
DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391.
Pale-yellow oil.
–
1
IR (KBr): 3476, 1685 cm .
(c) Woźniak, L. A.; Stec, W. J. Tetrahedron Lett. 1999, 40,
1
H NMR (300 MHz, CDCl ): d = 8.04 (d, J = 7.8 Hz, 1 H), 7.56–
2637. (d) Webb, K. S.; Levy, D. Tetrahedron Lett. 1995, 36,
5117. (e) Webb, K. S. Tetrahedron Lett. 1994, 35, 3457.
(f) Abu-Omar, M. M.; Espenson, J. H. Organometallics
1996, 15, 3543. (g) Curini, M.; Epifano, F.; Marcotullio,
M. C.; Rosati, O. Synlett 1999, 777. (h) Travis, B. R.;
Narayan, R. S.; Borhan, B. J. Am. Chem. Soc. 2002, 124,
3
7
1
1
.32 (m, 2 H), 7.28 (d, J = 6.9 Hz, 1 H), 4.39 (dd, J = 6.0, 13.5 Hz,
H), 3.92 (s, 1 H), 3.23–2.99 (m, 2 H), 2.59–2.49 (m, 1 H), 2.13–
.97 (m, 1 H).
1
3
C NMR (75 MHz, CDCl ): d = 199.6, 144.3, 134.2, 130.4, 128.9,
27.6, 12.9, 73.8, 31.8, 27.7.
3
1
3824.
MS (EI): m/z = 162, 144, 133, 118, 103, 90, 77.
(
13) (a) Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org.
Lett. 2005, 7, 2933. (b) Yakura, T.; Konishi, T. Synlett 2007,
765. (c) Schulze, A.; Giannis, A. Synthesis 2006, 257.
Anal. Calcd for C H O : C, 74.06; H, 6.21. Found: C, 74.13; H,
6
10
10
2
.10.
(
d) Bunton, C. A.; Foroudian, H. J.; Gillitt, N. D. J. Phys.
Org. Chem. 1999, 12, 758. (e) Frigerio, M.; Santagostino,
M.; Sputore, S. J. Org. Chem. 1999, 64, 4537. (f) Page,
P. C. B.; Appleby, L. F.; Buckley, B. R.; Allin, S. M.;
McKenzie, M. J. Synlett 2007, 1565.
Acknowledgment
The authors thank the State Key Laboratory of Applied Organic
Chemistry for financial support.
(
(
14) Schadt, F. L.; Bentley, T. W.; Schleyer, P. v. R. J. Am. Chem.
Soc. 1976, 98, 7667.
15) (a) Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.;
Tohma, H.; Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193.
(
b) Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221.
Synthesis 2008, No. 20, 3205–3208 © Thieme Stuttgart · New York