Chiral Lewis Acid-Mediated Enantioselective Pictet-Spengler Reaction of Nb-Hydroxytryptamine with Aldehydes

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6348-6354

  Yamada, Hideki ^a   Kawate, Tomohiko ^a   Matsumizu, Miyako ^a   Nishida, Atsushi ^a   Yamaguchi, Kentaro ^a   Nakagawa, Masako ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000489863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980810h     Document Type: Article

References (35)

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16. Recent reports: (a) Zhang, P.; Cook, J. M. Tetrahedron Lett. 1995, 36, 6999-7002 and references therein. (b) Waldmann, H.; Schmidt, G. Tetrahedron 1994, 50, 11865-11884. (c) Bailey, P. D.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 3587-3588. (d) Melnyk, P.; Ducrot, P.; Thal, C. Tetrahedron 1993, 49, 8589-8596. (e) Piper, I. M.; MacLean, D. B.; Kvarnström, I.; Szarek, W. A. Can. J. Chem. 1983, 61, 2721-2728.
17. Recent reports: (a) Zhang, P.; Cook, J. M. Tetrahedron Lett. 1995, 36, 6999-7002 and references therein. (b) Waldmann, H.; Schmidt, G. Tetrahedron 1994, 50, 11865-11884. (c) Bailey, P. D.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 3587-3588. (d) Melnyk, P.; Ducrot, P.; Thal, C. Tetrahedron 1993, 49, 8589-8596. (e) Piper, I. M.; MacLean, D. B.; Kvarnström, I.; Szarek, W. A. Can. J. Chem. 1983, 61, 2721-2728.
18. Recent reports: (a) Zhang, P.; Cook, J. M. Tetrahedron Lett. 1995, 36, 6999-7002 and references therein. (b) Waldmann, H.; Schmidt, G. Tetrahedron 1994, 50, 11865-11884. (c) Bailey, P. D.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 3587-3588. (d) Melnyk, P.; Ducrot, P.; Thal, C. Tetrahedron 1993, 49, 8589-8596. (e) Piper, I. M.; MacLean, D. B.; Kvarnström, I.; Szarek, W. A. Can. J. Chem. 1983, 61, 2721-2728.
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24. 24 + 15.6 (c 0.38, EtOH).
25. 24 - 52 (c 2.0, EtOH).
26. The calculated optical purity of 10 suggests partial racemization during zinc reduction of 9. A reduction procedure without racemization is being actively investigated.
27. The calculation was carried out using CAChe system Version 3.8, CAChe Scientific Inc., 1995.
28. A similar result was obtained from a semiempirical molecular orbital calculation of the cyclization of 8 from both the re- and si-faces of the C=N bond attacked by indole nuclei at the 3-position.
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32. w = 0.055.
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34. 2BCl.
35. Nakagawa, M.; Kawate, T.; Kakikawa, T.; Yamada, H.; Matsui, T.; Hino, T. Tetrahedron 1993, 49, 1739-1748.