196
C. Pasquier et al. / Tetrahedron: Asymmetry 9 (1998) 193–196
Acknowledgements
We are grateful to Dr. Jean-François Carpentier for helpful discussions. We thank the ‘Ministère de la
Recherche et de la Technologie’ and the CNRS for their financial support.
References
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(
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Tetrahedron: Asymmetry 1994, 5, 809. (c) Kündig, E. P.; Xu, L.-H.; Romanens, P.; Bernardelli, G. Synlett 1996, 270. (d)
Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
3
4. Togni, A.; Hayashi, T., Eds. In Ferrocenes; VCH Weinheim, 1995.
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. (a) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238. (b) Jones, G. B.; Heaton,
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6
7
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8
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1
9. 2: H NMR (300 MHz, CDCl
3
): δ 7.1 (d, J=7.3 Hz, 1H), 7.0 (t, J=7.6 Hz, 1H), 6.7 (d, J=7.3 Hz, 1H), 6.65 (d, J=7.6 Hz,
=10.7 Hz, J =3.5 Hz, 1H), 3.6 (dd, J =10.7 Hz, J =6.3 Hz, 1H), 3.1 (dd, J =15.9 Hz, J =9.0
=15.9 Hz, J ): δ 150.5, 128.9, 127.5, 124.9, 119.3, 110.1,
=7.9 Hz, 1H); 13C NMR (75.5 MHz, CDCl
): δ 5.6 (d, J=5.6 Hz, 1H), 5.4 (s, 1H), 5.0 (d, J=6.4 Hz, 1H), 4.8
1
H), 4.0 (m, 1H), 3.7 (dd, J
Hz, 1H), 2.8 (dd, J
5.2, 60.3, 32.1, 30.6. syn-3: H NMR (300 MHz, CDCl
1
2
1
2
1
2
1
2
3
1
6
(
3
1
3
s, 1H), 4.1 (m, 2H), 3.6 (d, J=7.3 Hz, 1H), 3.1 (dd, J
1
2
=10.3 Hz, J =14.4 Hz, 1H), 2.6 (d, J=14.4 Hz, 1H); C NMR (75.5
1
MHz, CDCl
3
): δ 237.4, 135.3, 98.7, 97.0, 96.0, 86.5, 76.2, 65.3, 60.5. anti-3: H NMR (300 MHz, CDCl
3
): δ 5.6 (d, J=5.3
1
3
Hz, 1H), 5.4 (s, 1H), 5.0 (d, J=5.5 Hz, 1H), 4.8 (s, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.6 (s, 1H), 2.8 (d, J=8.7 Hz, 1H);
NMR (75.5 MHz, CDCl ): δ 234.6, 133.1, 98.3, 94.6, 93.1, 84.5, 74.0, 63.9, 60.6, 30.6.
0. 31P{ H} NMR data at 121 MHz (ppm, CDCl
) 4: 114.2 (s, OPPh ), 41.6 (s, NPPh ); 5: 116.9 (s, OPPh
: 145.9 (s, OPCp ), 63 (s, NPCp ); 7: 146 (s, OPCp ), 67.3 (s, NPCp ).
C
3
1
1
3
2
2
2 2
), 43.1 (s, NPPh
);
6
2
2
2
2
1
1
1
1. Roucoux, A.; Agbossou, F.; Mortreux, A.; Petit, F. Tetrahedron: Asymmetry 1993, 4, 2279.
2. Devocelle, M.; Agbossou, F.; Mortreux, A. Synlett 1997, in press.
3. It would be premature to form conclusions regarding the relative effect on the selectivity of the chromium complexation
without extending the study to the other diastereomer and thus searching for the accessibility to the latter.