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A. Bierstedt et al. / Tetrahedron: Asymmetry 12 (2001) 3399–3407
1.32–1.44 (m, 2H), 1.83–1.90 (m, 3H), 1.90–2.17 (m,
2H), 3.44 (d, J=13.8 Hz, 1H), 3.51 (d, J=13.8 Hz,
1H), 3.87 (dd, J=5.0 Hz, J=7.9 Hz, 1H), 4.06 (d,
J=17.4 Hz, 1H), 4.13 (d, J=17.4 Hz, 1H), 6.24 (dd,
J=0.9 Hz, J=3.1 Hz, 1H), 6.31 (dd, J=1.9 Hz, J=3.1
Hz, 1H), 7.35 (dd, J=0.9 Hz, J=1.9 Hz, 1H). 13C
NMR (75.4 MHz, CDCl3): l 19.75 (q), 20.65 (q), 26.29
(t), 32.66 (t), 34.87 (t), 38.18 (t), 44.51 (d), 47.68 (s),
48.49 (s), 52.76 (t), 65.05 (d), 108.67 (d), 110.36 (d),
142.12 (d), 146.75 (s), 166.48 (s); MS (GC) m/z: 323
(41) [M+], 81 (100); anal. calcd for C16H21NO4S: C,
59.42; H, 6.54; N, 4.33. Found C, 59.40; H, 6.61; N,
4.51%.
Acknowledgements
The authors thank Professor Dr. W. Ko¨nig, Hamburg,
for valuable help with the chiral GC analyses. Gifts of
CHIRAZYM® ASL and PPL from Boehringer
Mannheim are greatly appreciated.
References
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1
IR (KBr): 1695, 1317, 1110 cm−1; H NMR (300 MHz,
CDCl3): l 0.97 (s, 3H), 1.18 (s, 3H), 1.33–1.44 (m, 2H),
1.58 (d, J=7.2 Hz, 3H), 1.87–2.10 (m, 5H), 3.45 (d,
J=13.8 Hz, 1H), 3.58 (d, J=13.8 Hz, 1H), 3.91 (dd,
J=5.3 Hz, J=7.4 Hz, 1H), 4.48 (q, J=7.2 Hz, 1H),
6.23 (dd, J=0.7 Hz, J=3.1 Hz, 1H), 6.30 (dd, J=1.9
Hz, J=3.1 Hz, 1H), 7.35 (dd, J=0.7 Hz, J=1.9 Hz,
1H). 13C NMR (75.4 MHz, CDCl3): l 17.09 (q), 19.85
(q), 20.83 (q), 26.39 (t), 32.83 (t), 38.29 (t), 39.83 (d),
44.62 (d), 47.79 (s), 48.43 (s), 53.04 (t), 65.31 (d), 106.96
(d), 110.13 (d), 141.97 (d), 152.32 (s), 171.97 (s); MS
(GC) m/z: 337 (13) [M+], 95 (100); anal. calcd for
C17H23NO4S: C, 60.51; H, 6.87; N, 4.15. Found C,
60.28; H, 7.06; N, 4.07%.
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3.10.3. (S)-2-(2%-Furyl)propan-1-ol (S)-2 by reduction of
7. To a suspension of LiAlH4 (67 mg, 1.77 mmol) in
dry THF (6 mL) was slowly added a solution of 7 (590
mg, 1.75 mmol) in dry THF (12 mL) at room tempera-
ture under argon. After stirring for 1 h at room temper-
ature, sat. aqueous Na2SO4 was added and the aqueous
layer extracted with ethyl acetate. The combined
organic extracts were dried over MgSO4 and concen-
trated in vacuo. The residue was treated with pentane
at −30°C, and (2R)-bornane-2,10-sultam 5 (318 mg,
84%) was separated from the solution of the alcohol by
filtration. After concentration of the pentane solution
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chromatography over silica gel (ether/petrol ether, 1:1)
to give (+)-(S)-2 (196 mg, 89%).
1995, 60, 6959–6969.
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23. X-Ray crystal structure analysis of 7: Formula
C17H23NO4S, M=337.42, colorless crystal 0.70×0.40×
,
0.30 mm, a=15.087(3), b=7.842(2), c=15.624(3) A, i=
3
g ,
cm−3
,
112.07(2)°, V=1713.1(6) A , zcalcd=1.308
v=18.45 cm−1, empirical absorption correction via c
scan data (0.3585T50.608), Z=4, monoclinic, space