Enantioselective asymmetric Pictet-Spengler reaction catalyzed by diisopinocampheylchloroborane

被引:41
作者
Kawate, T [1 ]
Yamada, H [1 ]
Soe, T [1 ]
Nakagawa, M [1 ]
机构
[1] CHIBA UNIV,FAC PHARMACEUT SCI,INAGE KU,CHIBA 263,JAPAN
关键词
D O I
10.1016/0957-4166(96)00134-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The first example of a reagent-controlled enantioselective Pictet-Spengler reaction is demonstrated. Employing diisopinocampheylchloroborane as a chiral Lewis acid catalyst, the Pictet-Spengler reaction of Nb-hydroxytryptamine gave the corresponding 2-hydroxy-tetrahydro-beta-carbolines up to 90 %ee. Copyright (C) 1996 Elsevier Science Ltd
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页码:1249 / 1252
页数:4
相关论文
共 21 条
[1]  
AKIMOTO H, 1974, CHEM PHARM BULL, V22, P2614
[2]   ENHANCING THE YIELD AND DIASTEREOSELECTIVITY OF THE PICTET-SPENGLER REACTION - A HIGHLY EFFICIENT ROUTE TO CIS-1,3-DISUBSTITUTED TETRAHYDRO-BETA-CARBOLINES [J].
BAILEY, PD ;
MOORE, MH ;
MORGAN, KM ;
SMITH, DI ;
VERNON, JM .
TETRAHEDRON LETTERS, 1994, 35 (21) :3587-3588
[3]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[4]   SYNTHESIS OF BIOACTIVE NITROGEN-HETEROCYCLES FROM MARINE ORGANISMS [J].
HINO, T ;
NAKAGAWA, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (03) :625-630
[5]  
HINO T, 1990, CHEM PHARM BULL, V38, P59
[6]  
KAWATE T, 1992, HETEROCYCLES, V33, P801
[7]  
KAWATE T, UNPUB
[8]   TOTAL SYNTHESIS OF (+)-FUMITREMORGIN-B, ITS EPIMERIC ISOMERS, AND DEMETHOXY DERIVATIVES [J].
KODATO, S ;
NAKAGAWA, M ;
HONGU, M ;
KAWATE, T ;
HINO, T .
TETRAHEDRON, 1988, 44 (02) :359-377
[9]  
LIU JJ, 1991, CHEM PHARM BULL, V39, P1672
[10]   SYNTHESIS OF THE 2 ENANTIOMERS OF A TETRAHYDRO-BETA-CARBOLINE FROM L-(-)-TRYPTOPHAN [J].
MASSIOT, G ;
MULAMBA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (20) :1147-1149