A novel stereoselective synthesis of (2Z)-2-arylsulfanylallylic alcohols by tin-lithium exchange of (E)-αstannylvinyl sulfides

Article abstract of DOI:10.1002/hc.20487

Tin-lithium exchange reaction of (E)-α-stannylvinyl sulfides 1 with n-butyllithium gave (Z)-α-arylsulfanylvinyllithiums 1, which reacted with aldehydes or ketones 3 to afford stereoselectively (2Z)-2-arylsulfanylallylic alcohols 4 in good to high yields.

Full text of DOI:10.1002/hc.20487

Heteroatom Chemistry
Volume 19, Number 6, 2008
A Novel Stereoselective Synthesis of
(2Z)-2-Arylsulfanylallylic Alcohols by
Tin–Lithium Exchange of (E)-α-Stannylvinyl
Sulfides
Yaping Xu,1,2 Wenyan Hao,1 Dong Wang,1 and Mingzhong Cai1
1Department of Chemistry, Jiangxi Normal University, Nanchang 330022,
People’s Republic of China
2Department of Chemistry, Jinggangshan University, Jian 343009, People’s Republic of China
Received 2 January 2007; revised 19 March 2008
substituted allylic alcohols has attracted much inter-
ABSTRACT: Tin–lithium exchange reaction of (E)-
est in organic chemistry [14–19]. Substituted allylic
α-stannylvinyl sulfides 1 with n-butyllithium gave
alcohols are usually prepared by the Reformatsky
(Z)-α-arylsulfanylvinyllithiums 2, which reacted with
reaction of the corresponding ketones [20], or by a
aldehydes or ketones 3 to afford stereoselectively
Horner–Wadsworth–Emmons reaction [21,22], but
(2Z)-2-arylsulfanylallylic alcohols 4 in good to high
a mixture of isomers is often obtained. Although
ꢀ
C
yields. 2008 Wiley Periodicals, Inc. Heteroatom Chem
substantial progress has been made in the synthesis
of (E)-di- and (E)-trisubstituted allylic alcohols [23–
27], the one-pot synthesis of (E)-2,3-disubstituted
19:639–643, 2008; Published online in Wiley InterScience
(www.interscience.wiley.com). DOI 10.1002/hc.20487
allylic alcohols remains a formidable challenge [28].
The stereocontrolled synthesis of allylic alcohols
INTRODUCTION
containing metal or heteroatom functional groups
is also of considerable interest in organic synthesis
because many useful functional group transforma-
tions can be achieved by introduction and removal
of metal or heteroatom functions. Lee and Kim
[29] reported efficient preparation of enantiomer-
ically pure (3E)-4-(tributylstannyl)but-3-en-2-ol by
lipase-mediated resolution. The stereoselective syn-
thesis of (2Z)-2-(butylseleno)allylic alcohols [30],
(2Z)-2-silylallylic alcohols [31], (2E)-3-silylallylic al-
cohols [32], (2E)-2-sulfonylallylic alcohols [33,34],
and (2Z)-2-arylselenoallylic alcohols [35] has also
been described in the literature. Recently, Huang
and Xie [36] reported an efficient synthesis of
(Z)-2,3-difunctionalized allylic alcohols by the
stereoselective Michael–Aldol tandem reaction of
phenylselenomagnesium bromide with acetylenic
sulfones and aldehydes. Silveira et al. [37] described
Stereodefined trisubstituted alkenes exist widely in
both natural and nonnatural products [1–5], but
their synthesis is still a challenging problem in syn-
thetic organic chemistry [6,7]. Disubstituted alco-
hols are among the most versatile intermediates in
organic synthesis [8,9] and are pervasive in natural
products and commercially important pharmaceuti-
cals [10–13]. Thus, the stereocontrolled synthesis of
Correspondence to: Mingzhong Cai; e-mail: caimzhong@163.
com.
Contract grant sponsor: National Natural Science Foundation
of China.
Contract grant number: 20462002.
Contract grant sponsor: Natural Science Foundation of Jiangxi
Province of China
Contract grant number: 0420015.
2008 Wiley Periodicals, Inc.
c
ꢀ
639

640 Xu et al.
SAr
SAr
Li
the synthesis of 2-alkylthioallylic alcohols by the
Te–Li exchange reaction of α-tellurenylvinyl sul-
fides with n-butyllithium, followed by treatment
with aldehydes, but the reaction was rather com-
plicated and a mixture of isomers was obtained.
Tanaka and coworkers [38] reported the synthesis
of (2Z)-2-phenylthio-3-methoxycarbonylallylic alco-
hols by palladium-catalyzed thioesterification of
alkynes with O-methyl S-phenyl thiocarbonate. Very
recently, Zeni and coworkers [39] described a highly
stereoselective one-pot procedure to prepare (2Z)-2-
phenylthio-3-phenylselenoallylic alcohols via addi-
tion of chalcogens to alkynes. Despite the availability
of synthetic methods of (2Z)-2-arylsulfanylallylic al-
cohols as described above, there still exists a need for
new selective and convenient procedures. Herein, we
wish to report that (2Z)-2-arylsulfanylallylic alcohols
could be conveniently synthesized in one pot by the
tin–lithium exchange reaction of (E)-α-stannylvinyl
sulfides with n-butyllithium, followed by the treat-
ment with aldehydes or ketones.
R
H
R
H
n-BuLi/THF
°
SnBu3
-
78 C
1
2
1
R
SAr
R
H
(3)
O
2
R
OH
°
78 C, THF
-
R1
R2
4
SCHEME 1
fides with high regio- and stereoselectivities and high
yields [40]. Investigations of the crude products 4
by H NMR spectroscope (400 MHz) showed their
1
isomeric purities to be more than 98%. The config-
uration of intermediates 2 could be confirmed from
compounds 5, which were obtained by hydrolysis
with aqueous NH4Cl (Scheme 2). The stereochem-
istry of compounds 5 was easily established, since
1H NMR spectra of 5a–b give rise to a doublet at
δ = 6.14 or 6.53 with a coupling constant of 9.2 or
10.8 Hz, which is consistent with a Z-configuration.
In addition, the Z-configuration of the compound
4c was confirmed by the nuclear Overhauser effect
spectroscopy (NOESY) in the 1H NMR spectrum. An
enhancement of the allylic protons was observed as
the vinylic proton (δ = 6.40) of 4c was irradiated. The
correlation between the allylic protons and aromatic
proton was also observed. There was no correlation
between the vinylic proton (δ = 6.40) and aromatic
proton. The nuclear Overhauser effect (NOE) results
indicate that 4c has the expected Z-configuration.
In summary, a convenient one-pot synthetic
method for (2Z)-2-arylsulfanylallylic alcohols has
been developed by tin–lithium exchange reaction of
RESULTS AND DISCUSSION
(E)-α-Stannylvinyl sulfides 1 were prepared regio-
and stereoselectively by the palladium-catalyzed
hydrostannylation reaction of alkynylsulfides ac-
cording to a literature procedure [40]. (E)-α-
Stannylvinyl sulfides 1 are very useful difunctional
group reagents in which two synthetically versatile
groups are linked to the same olefinic carbon
atom and can be considered both as vinylstan-
nanes and as vinyl sulfides. Vinylstannanes can
undergo the tin–lithium exchange reaction with n-
butyllithium to afford the corresponding vinyllithi-
ums with the retention of the configuration [41,42].
With a convenient route to the (E)-α-stannylvinyl
sulfides 1, we decided to establish the feasibility
of using 1 in tin–lithium exchange reactions with
n-butyllithium. We observed that the tin–lithium
exchange reaction of (E)-α-stannylvinyl sulfides
1
with n-butyllithium at −78◦C in THF for
TABLE 1 Synthesis of (2Z)-2-Arylsulfanylallylic Alcohols
4a–j
30 min gave (Z)-α-arylsulfanylvinyllithiums 2,
which reacted with aldehydes or ketones
3
R
Ar
R1
R2 Product Yield (%)a
to afford stereoselectively the desired (2Z)-2-
arylsulfanylallylic alcohols 4 (Scheme 1). Typical re-
sults are summarized in Table 1.
n-C4H9
n-C4H9
n-C4H9
n-C4H9
Ph
CH3OCH2
Ph
n-C4H9
CH3OCH2
CH3OCH2
Ph
4-CH3C6H4
4-CH3C6H4
Ph
Ph
Ph
CH3
Ph
Ph
CH3
CH3
H
H
4a
4b
4c
4d
4e
4f
83
88
76
85
82
87
81
76
87
83
CH3
CH3
CH3
CH3
CH3
H
As shown in Table 1, both a variety of aldehy-
des and ketones could react rapidly with the inter-
mediates 2 at −78◦C to afford the corresponding
(2Z)-2-arylsulfanylallylic alcohols 4 in good to high
yields. This methodology for (2Z)-2-arylsulfanyl-
allylic alcohols has a large scope because a variety
of (E)-α-stannylvinyl sulfides can be conveniently
prepared by the hydrostannylation of alkynylsul-
Ph
Ph
4-CH3C6H4
4-CH3C6H4 n-C6H13
4g
4h
4i
Ph
Ph
n-C6H13
—(CH2)5—
H
4j
aIsolated yield based on the (E)-α-stannylvinyl sulfide 1 used.
Heteroatom Chemistry DOI 10.1002/hc

A Novel Stereoselective Synthesis of (2Z)-2-Arylsulfanylallylic Alcohols 641
(22), 189 (39), 149 (66), 105 (75), 91 (82), 77 (100);
Anal. Found: C, 76.28; H, 7.14. C19H22OS Calcd: C,
76.46; H, 7.43%.
SAr
Li
R
H
SAr
H
R
H
H2O
°
-
78 C
5a: R = n-C4H9, Ar= 4-CH 3C6H4, 90%
5b: R = Ph, Ar= 4-CH 3C6H4, 87%
2
(Z)-1-Phenyl-2-(4-methylphenyl)sulfanyl-2-
hepten-1-ol 4b. IR (film) ν (cm−1): 3417, 3062, 3029,
2957, 2925, 1715, 1632, 1600, 1491, 1454, 1086, 910,
SCHEME 2
1
806, 699; H NMR (400 MHz, CDCl3) δ: 7.32–7.26
(m, 5H), 7.14 (d, J = 8.0 Hz, 2H), 7.05 (d, J = 8.0 Hz,
2H), 6.27 (t, J = 7.2 Hz, 1H), 5.17 (s, 1H), 2.38–2.30
(m, 6H), 1.40–1.25 (m, 4H), 0.87 (t, J = 7.2 Hz, 3H);
13C NMR (100 MHz, CDCl3) δ: 141.8, 139.1, 136.0,
135.7, 131.7, 129.8, 129.0, 128.3, 127.7, 126.7, 76.5,
31.1, 29.5, 22.4, 21.0, 13.9; MS m/z: 312 (M+, 4.6),
189 (100), 163 (31), 129 (53), 105 (64), 91 (84), 77
(47); Anal. Found: C, 76.60; H, 7.49. C20H24OS Calcd:
C, 76.88; H, 7.74%.
(E)-α-stannylvinyl sulfides with n-butyllithium, fol-
lowed by treatment with aldehydes or ketones. Com-
pared with the method reported [37], this methodol-
ogy has the advantages of readily available starting
materials, straightforward and simple procedures,
high stereoselectivity, and high yields.
EXPERIMENTAL
THF was distilled from sodium benzophenone ketyl
prior to use. IR spectra were obtained on a Perkin–
Elmer 683 instrument as neat films. 1H NMR spectra
were recorded on a Bruker AC-400 (400 MHz) spec-
trometer with TMS as an internal standard using
CDCl3 as solvent. 13C NMR spectra were recorded
on a Bruker AC-400 (100 MHz) spectrometer using
CDCl3 as solvent. Mass spectra were determined on
a Finnigan 8230 mass spectrometer. Microanalyses
were measured using a Yanaco MT-3 CHN microele-
mental analyzer.
(Z)-2-Methyl-3-(4-methylphenyl)sulfanyl-3-octen-
2-ol 4c. IR (film) ν (cm−1): 3460, 3076, 3031, 2956,
2925, 1628, 1596, 1491, 1467, 1361, 971, 825, 801;
1H NMR (400 MHz, CDCl3) δ: 7.10 (d, J = 8.0 Hz,
2H), 7.03 (d, J = 8.0 Hz, 2H), 6.40 (t, J = 7.2 Hz,
1H), 2.35 (br, 1H), 2.28 (s, 3H), 2.26–2.20 (m, 2H),
1.41 (s, 6H), 1.37–1.22 (m, 4H), 0.84 (t, J = 7.2 Hz,
3H); 13C NMR (100 MHz, CDCl3) δ: 139.5, 138.1,
134.9, 133.5, 129.6, 126.7, 74.3, 31.0, 30.2, 29.4,
22.4, 20.9, 13.9; MS m/z: 264 (M+, 7.1), 91 (48), 71
(62), 57 (100), 43 (98); Anal. Found: C, 72.41; H,
8.87. C16H24OS Calcd: C, 72.67; H, 9.15%.
General Procedure for the Synthesis of
(2Z)-2-Arylsulfanylallylic Alcohols 4a–j
(Z)-2-Phenyl-3-phenylsulfanyl-3-octen-2-ol
4d.
IR (film) ν (cm−1): 3475, 3059, 3025, 2957, 2929,
1687, 1599, 1582, 1478, 1447, 1266, 760, 739, 700;
1H NMR (400 MHz, CDCl3) δ: 7.48–7.17 (m, 10H),
6.43 (t, J = 6.8 Hz, 1H), 3.01 (s, 1H), 2.31–2.26 (m,
1H), 2.18–2.14 (m, 1H), 1.75 (s, 3H), 1.39–1.21 (m,
4H), 0.84 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ: 146.4, 139.4, 138.8, 136.8, 128.8, 128.3,
128.2, 127.0, 125.5, 125.3, 78.1, 30.8, 30.2, 28.8, 22.5,
13.9; MS m/z: 312 (M+, 3.8), 192 (100), 149 (54), 110
(61), 77 (33), 43 (43); Anal. Found: C, 76.71; H, 7.87.
C20H24OS Calcd: C, 76.88; H, 7.74%.
To a solution of (E)-α-stannylvinyl sulfide 1 (0.5
mmol) in THF (5 mL) at −78◦C under argon, a solu-
tion of n-BuLi (0.2 mL, 0.5 mmol, 2.5 M solution in
hexane) was added dropwise. After 30 min of stirring
at this temperature, aldehyde or ketone (0.6 mmol)
was added. The mixture was stirred for 1 h at −78◦C,
then diluted with ethyl acetate (20 mL) and washed
with brine (4 × 10 mL). The organic layer was sep-
arated and dried over MgSO4, and the solvent was
removed under vacuum. The residue was purified by
column chromatography on silica gel (eluent: light
petroleum ether/EtOAc, 10:1).
(Z)-2,4-Diphenyl-3-phenylsulfanyl-3-buten-2-ol
4e. IR (film) ν (cm−1): 3433, 3059, 3025, 2957,
2931, 1719, 1600, 1582, 1493, 1445, 1026, 763, 739,
(Z)-1-Phenyl-2-phenylsulfanyl-2-hepten-1-ol 4a.
IR (film) ν (cm−1): 3410, 3061, 3029, 2957, 2928,
1714, 1632, 1582, 1477, 1454, 1024, 909, 738, 699;
1H NMR (400 MHz, CDCl3) δ: 7.33–7.13 (m, 10H),
6.36 (t, J = 7.2 Hz, 1H), 5.20 (s, 1H), 2.37–2.31 (m,
2H), 2.18 (br, 1H), 1.41–1.25 (m, 4H), 0.87 (t, J = 7.2
Hz, 3H); 13C NMR (100 MHz, CDCl3) δ: 141.7, 140.0,
135.6, 135.1, 129.0, 128.4, 128.3, 127.8, 126.7, 125.9,
76.8, 31.1, 29.5, 22.4, 13.9; MS m/z: 298 (M+, 5.2), 280
1
699; H NMR (400 MHz, CDCl3) δ: 7.59–7.05 (m,
16H), 3.20 (s, 1H), 1.89 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 148.1, 146.1, 135.2, 129.4, 128.7, 128.3,
128.1, 128.0, 127.6, 127.4, 126.5, 125.7, 125.6, 124.8,
78.8, 30.2; MS m/z: 332 (M+, 6.3), 280 (61), 212 (97),
178 (31), 115 (56), 91 (76), 77 (61), 43 (100); Anal.
Found: C, 79.27; H, 5.87. C22H20OS Calcd: C, 79.48;
H, 6.06%.
Heteroatom Chemistry DOI 10.1002/hc

642 Xu et al.
2853, 1716, 1629, 1582, 1478, 1439, 1121, 739, 690;
1H NMR (400 MHz, CDCl3) δ: 7.27–7.20 (m, 4H),
7.14–7.10 (m, 1H), 6.53 (t, J = 5.6 Hz, 1H), 4.05 (d,
J = 5.6 Hz, 2H), 3.27 (s, 3H), 1.90 (br, 1H), 1.76–1.56
(m, 10H); 13C NMR (100 MHz, CDCl3) δ: 141.9,
136.5, 134.7, 129.1, 126.6, 125.4, 74.9, 71.3, 58.5,
36.1, 25.5, 21.9; MS m/z: 279 (M+ + 1, 5.2), 261 (38),
152 (95), 110 (53), 91 (100), 71 (57); Anal. Found: C,
68.74; H, 7.87. C16H22O2S Calcd: C, 69.02; H, 7.97%.
(Z)-2-Methyl-3-phenylsulfanyl-5-methoxy-3-
penten-2-ol 4f. IR (film) ν (cm−1): 3431, 3059, 2976,
2927, 1715, 1582, 1478, 1455, 1371, 1185, 1121, 825,
1
740, 691; H NMR (400 MHz, CDCl3) δ: 7.27–7.21
(m, 4H), 7.15–7.13 (m, 1H), 6.54 (t, J = 5.2 Hz, 1H),
4.05 (d, J = 5.2 Hz, 2H), 3.28 (s, 3H), 2.30 (br, 1H),
1.45 (s, 6H); 13C NMR (100 MHz, CDCl3) δ: 141.5,
136.2, 134.3, 129.1, 126.8, 125.6, 74.2, 71.2, 58.5,
29.0; MS m/z: 238 (M+, 6.4), 220 (12), 110 (57),
91 (49), 77 (42), 45 (76), 43 (100); Anal. Found: C,
65.21; H, 7.47. C13H18O2S Calcd: C, 65.51; H, 7.61%.
General Procedure for the Synthesis of
(Z)-Vinyl Sulfides 5a–b
(Z)-2-Methyl-3-(4-methylphenyl)sulfanyl-4-
phenyl-3-buten-2-ol 4g. IR (film) ν (cm−1): 3325,
3078, 3022, 2986, 2921, 1626, 1597, 1490, 1446,
To
a solution of (E)-α-stannylvinyl sulfide 1
(0.5 mmol) in THF (5 mL) at −78◦C under argon
was added dropwise a solution of n-BuLi (0.2 mL,
0.5 mmol, 2.5 M solution in hexane). After 30 min
of stirring at this temperature, the mixture was hy-
drolyzed with saturated aq. NH4Cl (5 mL) and ex-
tracted with Et2O (2 × 20 mL). The organic extract
was washed with water (2 × 10 mL), dried with
MgSO4, filtered and concentrated under vacuum.
The residue was purified by column chromatogra-
phy on silica gel eluting with light petroleum ether.
1
1358, 971, 799, 691; H NMR (400 MHz, CDCl3) δ:
7.62–7.59 (m, 2H), 7.41 (s, 1H), 7.26–7.19 (m, 3H),
7.08 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 8.4 Hz, 2H),
2.37 (br, 1H), 2.28 (s, 3H), 1.52 (s, 6H); 13C NMR
(100 MHz, CDCl3) δ: 140.3, 135.9, 135.3, 135.0,
132.7, 129.6, 129.4, 128.0, 127.9, 127.3, 75.5, 29.6,
20.9; MS m/z: 284 (M+, 11.5), 266 (17), 124 (27),
91 (52), 77 (39), 43 (100); Anal. Found: C, 75.78; H,
6.86. C18H20OS Calcd: C, 76.01; H, 7.09%.
(Z)-1-Hexyl-2-(4-methylphenyl)sulfanyl-2-hepten-
(Z)-1-(4-Methylphenyl)sulfanyl-1-hexene 5a. IR
(film) ν (cm−1): 3074, 2958, 2926, 1716, 1609, 1493,
1459, 1376, 806, 690; H NMR (400 MHz, CDCl3) δ:
1-ol 4h. IR (film) ν (cm−1): 3410, 3019, 2956, 2927,
1
1
1713, 1632, 1492, 1457, 806; H NMR (400 MHz,
CDCl3) δ: 7.17 (d, J = 8.0 Hz, 2H), 7.06 (d, J = 8.0
Hz, 2H), 6.23 (t, J = 7.2 Hz, 1H), 4.08 (t, J = 6.4
Hz, 1H), 2.37-2.29 (m, 5H), 1.82 (br, 1H), 1.66–1.54
(m, 2H), 1.40–1.21 (m, 12H), 0.90–0.85 (m, 6H);
13C NMR (100 MHz, CDCl3) δ: 138.6, 135.8, 135.7,
132.3, 129.7, 128.5, 75.6, 36.3, 31.8, 31.2, 29.4, 29.1,
25.7, 22.6, 22.4, 21.0, 14.1, 13.9; MS m/z: 320 (M+,
99), 302 (59), 259 (63), 236 (96), 231 (76), 161 (81),
124 (100), 91 (96), 55 (88); Anal. Found: C, 74.83; H,
9.79. C20H32OS Calcd: C, 74.94; H, 10.06%.
7.24 (d, J = 8.0 Hz, 2H), 7.10 (d, J = 8.0 Hz, 2H),
6.14 (d, J = 9.2 Hz, 1H), 5.75 (dt, J = 9.2, 7.2 Hz,
1H), 2.32 (s, 3H), 2.27–2.19 (m, 2H), 1.36–1.23 (m,
4H), 0.89 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ: 136.2, 132.9, 132.6, 129.7, 129.3, 123.6,
31.2, 29.4, 22.4, 21.0, 14.0; Anal. Found: C, 75.39;
H, 8.72. C13H18S Calcd: C, 75.67; H, 8.79%.
(Z)-1-Phenyl-2-(4-methylphenyl)sulfanylethene
5b. IR (film): ν (cm−1) 3073, 2973, 1607, 1590,
1564, 1492, 846, 811, 731; 1H NMR (400 MHz,
CDCl3) δ: 7.54–7.51 (m, 2H), 7.40–7.15 (m, 5H),
7.14 (d, J = 8.0 Hz, 2H), 6.53 (d, J = 10.8 Hz, 1H),
6.47–6.43 (m, 1H), 2.33 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 137.5, 136.6, 132.7, 130.6, 130.0, 128.8,
128.4, 127.1, 127.0, 126.5, 21.2; Anal. Found: C,
79.42; H, 6.05. C15H14S Calcd: C, 79.60; H, 6.23%.
(Z)-1-Hexyl-2-phenylsulfanyl-4-methoxy-2-buten-
1-ol 4i. IR (film): ν (cm−1): 3427, 3059, 2927, 2856,
1716, 1637, 1583, 1478, 1456, 1377, 1194, 1120, 741,
1
691; H NMR (400 MHz, CDCl3) δ: 7.30–7.24 (m,
4H), 7.20–7.16 (m, 1H), 6.38 (t, J = 5.6 Hz, 1H),
4.28–4.23 (m, 1H), 4.14–4.08 (m, 2H), 3.33 (s, 3H),
1.92 (br, 1H), 1.73–1.66 (m, 1H), 1.59–1.52 (m, 1H),
1.39–1.18 (m, 8H), 0.86 (t, J = 6.8 Hz, 3H); 13C NMR
(100 MHz, CDCl3) δ: 138.8, 134.9, 133.8, 129.1,
128.8, 126.3, 74.7, 70.2, 58.4, 36.2, 31.7, 29.1, 25.6,
22.6, 14.1; MS m/z: 294 (M+, 34), 205 (64), 167 (82),
135 (85), 109 (84), 71 (100), 55 (80); Anal. Found: C,
69.06; H, 8.87. C17H26O2S Calcd: C, 69.34; H, 8.90%.
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Heteroatom Chemistry DOI 10.1002/hc

A Novel Stereoselective Synthesis of (2Z)-2-Arylsulfanylallylic Alcohols 643
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Heteroatom Chemistry DOI 10.1002/hc