References
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2000,
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<A NAME="RD10802ST-7">7</A>
The t-butyl, p-tolyl and 2-pyridyl sulfoxides 1a,b,c,e,f were prepared by reacting the thiols
with the benzyl halides in refluxing acetone in the presence of
K2CO3, and oxidising the resulting sulfides
using NaIO4 in aq methanol. The 2,4-dimethoxyphenyl p-methoxybenzyl sulfoxide 1d was obtained
from the reaction of p-methoxybenzylmagnesium chloride
with 2,4-dimethoxybenzenesulfinyl chloride,
[25]
in THF
at 0 °C.
<A NAME="RD10802ST-8">8</A>
Dauksas V.
Gaidelis P.
Petrauskas O.
Udrenaite S.
Gasperaviciene G.
Ragoutiene N.
Khim. Farm. Zh.
1987,
21:
569
<A NAME="RD10802ST-9">9</A>
Typical Procedure
for Conjugate Addition: A solution of the sulfoxide 1b (0.50 g, 2.22 mmol) in THF (12 mL) at
-78 °C
was added dropwise via cannula to a solution of LDA, formed from
diisopropylamine (0.76 mL, 5.42 mmol) and 2.5 M BuLi in hexanes
(2.08 mL, 5.2 mmol) in THF (20 mL), at -78 °C.
After 15 min, a solution of the ester 11a (1.09
g, 5.34 mmol) in THF (4 mL) at -78 °C
was added, also via cannula. After a further 30 min, the reaction
was quenched with sat. aq NH4C1 (7 mL) and the mixture
was warmed to r.t. The suspension was poured into water (10 mL)
and extracted with CH2Cl2 (3 × 30
mL). The combined extracts were dried over MgSO4 and
concentrated in vacuo. The crude product was purified using flash
column chromatography on silica (1:1 petrol:ethyl acetate) to give (RS)-ethyl 3-[(lSR, SRS)-tert-butylsulfinyl-(4-methoxy-phenyl)methyl]-5-phenylpentanoate 12a, as an off white solid (0.72 g, 1.68
mmol, 74%), mp 95-96 °C. IR
(KBr): 2941, 1732, 1610, 1511, 1258, 1177, 1039 cm-1. 1H
NMR (CDCl3, 300 MHz): δ = 1.06
(s, 9 H, t-Bu), 1.23 (t, J = 7.2 Hz,
3 H, OEt), 1.60-1.80 (m, 2 H, H-4), 2.06 (dd, J = 10.8, 16.2
Hz, 1 H, H-2), 2.70-2.79 (m, 2 H, H-5), 2.94 (dd, J = 3.5, 16.2
Hz, 1 H, H-2), 2.94-3.02 (m, partially obscured, 1 H, H-3),
3.80 (s, 3 H, OMe), 4.04 (d, J = 3.5
Hz, 1 H, SCH), 4.09-4.13 (m, 2 H, OEt), 6.86 (d, J = 8.8 Hz,
2 H, H3′,H5′), 7.13-7.27 (m, 7 H, Ar-H). 13C
NMR (CDCl3, 67.5 MHz): δ = 14.22
(OEt), 23.85 (C(CH3)3), 33.57 (C-5), 33.80,
35.56, 36.03 (C-3), 55.27 (OCH3), 55.70 (CMe3), 60.52
(OEt), 61.96 (SCH), 114.19 (C-3′,C-5′), 125.93
(CAr), 126.15 (CAr), 128.37 (CAr),
128.41 (CAr), 131.02 (C-2′, C-6′), 141.87
(CAr), 159.31 (C-4′), 172.35 (C=O).
Anal. Calcd for C25H34O4S: C, 69.77;
H, 7.91; S, 7.44. Found: C, 69.85; H, 7.97; S, 7.80.
<A NAME="RD10802ST-10A">10a</A>
Ohno A.
Higaki M.
Rev.
Heteroatom. Chem.
1995,
13:
1
<A NAME="RD10802ST-10B">10b</A>
Boche G.
Lohrenz JCW.
Cioslowski J.
Koch W. In
The Chemistry of Sulphur-Containing Functional Groups
Patai S.
Rappoport Z.
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1993.
p.339
<A NAME="RD10802ST-11">11</A>
Ziegler FE.
Schwartz JA.
J. Org. Chem.
1978,
43:
985
<A NAME="RD10802ST-12A">12a</A>
Murphy WS.
Wattanasin S.
J.
Chem. Soc., Perkin Trans. 1
1982,
1029
<A NAME="RD10802ST-12B">12b</A>
Murphy WS.
Wattansasin S.
J. Chem.
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1982,
271
<A NAME="RD10802ST-12C">12c</A>
Murphy WS.
Wattanasin S.
J. Chem.
Soc., Perkin Trans. 1
1981,
2920
<A NAME="RD10802ST-13">13</A>
Typical Procedure
for Cyclisation: A solution of the sulfoxide 12a (1.31
g, 3.04 mmol) in nitromethane (32 mL) was cooled to 0 °C
under N2. Tin tetrachloride (0.44 mL, 3.79 mmol) was
added dropwise and the solution was heated at 50 °C
for 90 min. Aq NaOH (5%, 15 mL) was added, the solution
was extracted with CH2Cl2 (2 × 100
mL), and the combined organic extracts were washed with water (2 × 80 mL).
The organic layer was dried over MgSO4 and con-centrated
in vacuo. The crude product was purified using flash column chromatography
on silica (80:20 petrol:ethyl acetate) to give (1RS,
2SR)-ethyl l-(4-methoxyphenyl)-l,2,3,4-tetrahydro-2-naphthaleneacetate 13a, as a yellow solid (705 mg, 2.18 mmol,
72%), mp 84-85 °C. IR (KBr): 2912,
1727, 1513, 1240, 1124, 1021, 809 cm-1. 1H
NMR (CDCl3, 300 MHz): δ = 1.22
(t, J = 7.0
Hz, 3 H, OEt), 1.57-1.62 (m, 1 H, H-3), 2.02-2.08
(m, 1 H, H-3), 2.17 (dd, J = 10.0,
16.7 Hz, 1 H, CHCO2Et), 2.36-2.43 (m, 2 H, H-2, CHCO2Et),
2.90-2.99 (m, 2 H, H-4), 3.74 (d, J = 8.5
Hz,
1 H, H-1), 3.78 (s, 3 H, OCH3), 4.07 (q, J = 7.0 Hz,
2 H, OEt), 6.74 (d, J = 7.6
Hz, 1 H, H-8), 6.82 (d, J = 8.8
Hz, 2 H, H-3′, H-5′), 6.96-7.04 (m, 3
H, H-5, H-2′, H-6′), 7.06-7.11 (m, 2
H, H-6, H-7). 13C NMR (CDCl3,
75 MHz): δ = 14.25 (OEt), 27.06
(C-3), 28.51 (C-4), 38.94 (CH2CO2Et), 39.14 (C-2),
50.56 (C-1), 55.22 (OCH3), 60.21 (OEt), 113.76, 125.79,
125.83, 128.64, 130.33, 130.48, 136.58, 137.52, 139.17, 158.13,
172.99 (C=O). Anal. Calcd for C21H24O3:
C, 77.78; H, 7.41. Found: C, 77.72; H, 7.53. MS (EI): m/z (rel. intensity) = 324
(9) [M+], 236 (100), 201 (8),
121 (13), 29 (8).
(1
SR
, 2
RS
, 3
SR
)-Methyl 7,8-dimethoxy-1-(3,4-dimethoxyphenyl)-2-benzyloxymethyl-1,2,3,4-tetra-hydronaphthalene-3-carboxylate(16): IR absorption: IR (KBr): 3010, 2930,
1730, 1244, 1027 cm-1. 1H
NMR (CDCl3, 500 MHz): δ = 2.75
(1 H, m, H-2), 2.92 (ddd, J = 3.0
5.5, 9.0 Hz, 1 H, H-3), 2.98-3.00 (m, 2 H, H2-4), 3.40-3.50
(m, 2 H, CH2OBn), 3.55 (s, 3 H, OCH3), 3.71
(s, 3 H, OCH3), 3.80 (s, 3 H, OCH3), 3.84
(s, 3 H, OCH3), 3.88 (s, 3 H, OCH3), 4.19
(d, J = 3.2
Hz, 1 H, H-1), 4.45 (d, J = 12.1
Hz, 1 H, OCH2Ph), 4.47 (d, J = 12.1
Hz, 1 H, OCH2Ph), 6.41 (dd, J = 2.1,
8.4 Hz, 1 H, Ar-H), 6.42 (1 H, s, H-9), 6.61 (d, J = 2.1
Hz, 1 H, Ar-H), 6.64 (1 H, s, H-6), 6.73 (d, J = 8.4
Hz, 1 H, Ar-H). Anal. Calcd for C30H34O7:
C, 71.2; H, 6.7. Found: C, 71.4; H, 6.4. MS (EI): m/z (rel. intensity) = 506
(7) [M+], 385 (22), 325 (12),
91 (100).
(1
RS, 2
SR, 3
RS
)-Methyl 3-(4-methoxyphenyl)-2-phenylindan-1-carboxylate(19): IR (KBr): 2946, 1735, 1512, 1246,
1169, 1034, 744 cm-1. 1H
NMR (CDCl3, 300 MHz): δ = 3.75
(s, 3 H, OMe), 3.76 (s, 3 H, OMe), 3.98 (apparent t, J = 10.3 Hz,
1 H, H-2), 4.35 (d, J = 10.0
Hz, 1 H, H-3), 4.38 (d, J = 10.3
Hz, 1 H, H-1), 6.79 (d, J = 8.8
Hz, 2 H, Ar-H), 6.89 (dd, J = 1.2,
7.3 Hz, 1 H, H-7). 7.02 (d, J = 8.8
Hz, 2 H, Ar-H), 7.20-7.30 (m, 7 H, Ar-H), 7.38 (1 H, dd, J = 1.2, 7.0
Hz, Ar-H). 13C NMR (CDCl3,
75 MHz): δ = 52.39 (C-2) 55.43
(OMe), 56.92 (OMe), 58.21, 59.78, 114.10, 124.06, 125.46, 127.14,
127.65, 128.2, 128.33, 128.73, 129.88, 134.61, 140.02, 141.21 146.05,
172.99.
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<A NAME="RD10802ST-15">15</A> Unsaturated ester 11b was
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