2228
X. Jiang et al. / Tetrahedron: Asymmetry 15 (2004) 2223–2229
Purification by column chromatography (silica gel, ethyl
acetate/hexane 4:1) afforded the product as a colorless
oil (37%). H NMR (200 MHz, CDCl ) 2.92 (s, 3H), 3.06
3
13. (a) Haynes, R. K.; Au-Yeung, T. L.; Chan, W. K.; Lam,
W. L.; Li, Z. Y.; Yeung, L. L.; Chan, A. S. C.; Li, P.;
Koen, M.; Mitchell, C. R.; Vonwiller, S. C. Eur. J. Org.
Chem. 2000, 3205; (b) Haynes, R. K.; Lam, W. W.; Yeung,
L. L. Tetrahedron Lett. 1996, 37, 4729; (c) Haynes, R. K.;
Lam, W. W.; Williams, I. D.; Yeung, L. L. Chem. Eur. J.
1
(
1
s, 3H), 4.99 (d, J ¼ 1:8 Hz, 1H), 5.38 (d, J ¼ 1:8 Hz,
13
3
H), 7.25–7.46 (m, 5H); C NMR (50MHz, CDCl )
3
6.2, 36.5, 101.4, 124.7, 128.3, 128.5, 134.9, 153.2, 154.3;
þ
1
997, 3, 2052; (d) Kawashima, T.; Iwanga, H.; Okazaki,
ESI-MS m=z 51 (6), 72 (100), 103 (7), 191 (34) [M ];
HRMS (ESI ) calculated for C11
found: 191.09530.
R. Chem. Lett. 1993, 1531; (e) Kawashima, T.; Iwanga,
H.; Okazaki, R. Heteroatom Chem. 1995, 6, 235.
14. Van Leeuwen, P. W. N. M.; Roobeek, C. F. In Homoge-
neous Transition Metal Catalyzed Reactions. Advances in
Chemistry Series 230; American Chemical Society: Wash-
ington, DC, 1992; p 367.
þ
2
H13NO : 191.09461,
1
5. (a) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36,
657; (b) Jiang, X.-b.; Minnaard, A. J.; Feringa, B. L.; de
Vries, J. G. J. Org. Chem. 2004, 69, 2327.
Acknowledgements
8
T. Tiemersma is gratefully acknowledged for the assis-
tance with GC separations. Dr. D. Pe n~ a is acknowl-
edged for a gift of substrates.
16. Cobley, C. J.; van den Heuvel, M.; Abbadi, A.; de Vries,
J. G. Tetrahedron Lett. 2000, 41, 2467.
17. (a) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem.
2
001, 66, 8677; (b) Li, G. Y.; Fagan, P. J.; Watson, P. L.
Angew. Chem., Int. Ed. 2001, 40, 1513; (c) Li, G. Y. (Du
Pont de Nemours and Company, USA). U.S. Patent
6,124,462, 2000; (d) Li, G. Y. (Du Pont de Nemours and
Company, USA). U.S. Patent 6,291,722 B1, 2001.
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