Diastereoselective addition of chiral azomethine ylides to cinnamoyl moieties, attached to chiral auxiliaries

被引:23
作者
Karlsson, S [1 ]
Högberg, HE [1 ]
机构
[1] Mid Sweden Univ, Dept Nat & Environm Sci, SE-85170 Sundsvall, Sweden
关键词
D O I
10.1016/S0957-4166(01)00366-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Doubly diastercoselective 1.3-dipolar cycloadditions of chiral azomethine ylides to cinnamoyl moieties, attached to chiral auxiliaries, were investigated. The resulting trans-3.4-disubstituted pyrrolidines were obtained in diastereomeric ratios of up to 78:22. The influence on this ratio by the constitution of the chiral ylide,vas found to be rather small. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1975 / 1976
页数:2
相关论文
共 9 条
[1]   DIASTEREOSELECTIVE AZOMETHINE YLIDE CYCLOADDITIONS TO UNSATURATED, CHIRAL BICYCLIC LACTAMS [J].
FRAY, AH ;
MEYERS, AI .
TETRAHEDRON LETTERS, 1992, 33 (25) :3575-3578
[2]   Single and double diastereoselection in azomethine ylide cycloaddition reactions with unsaturated chiral bicyclic lactams [J].
Fray, AH ;
Meyers, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3362-3374
[3]   Asymmetric 1,3-dipolar cycloaddition reactions [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (02) :863-909
[4]  
Karlsson S, 2001, ORG PREP PROCED INT, V33, P105
[5]   trans-3,4-disubstituted pyrrolidines by 1,3-dipolar cycloaddition:: enantioselective approaches and their limitations [J].
Karlsson, S ;
Han, F ;
Högberg, HE ;
Caldirola, P .
TETRAHEDRON-ASYMMETRY, 1999, 10 (13) :2605-2616
[6]  
LOWN JW, 1984, 1 3 DIPOLAR CYCLOADD, V1
[7]   Asymmetric dipolar cycloaddition reactions: A practical, convergent synthesis of chiral pyrrolidines [J].
Ma, ZK ;
Wang, SY ;
Cooper, CS ;
Fung, AKL ;
Lynch, JK ;
Plagge, F ;
Chu, DTW .
TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :883-887
[8]   CAMPHOR AS A NATURAL SOURCE OF CHIRALITY IN ASYMMETRIC-SYNTHESIS [J].
OPPOLZER, W .
PURE AND APPLIED CHEMISTRY, 1990, 62 (07) :1241-1250
[9]  
Wittland C, 1997, SYNTHESIS-STUTTGART, P1291