HIGHLY EFFECTIVE DIASTEREODIFFERENTIATION OF MESO-DICARBOXYLIC ANHYDRIDES USING STERICALLY CONGESTED CHIRAL N-SULFONYLAMINOALCOHOLS

被引:30
作者
IMADO, H [1 ]
ISHIZUKA, T [1 ]
KUNIEDA, T [1 ]
机构
[1] KUMAMOTO UNIV,FAC PHARMACEUT SCI,KUMAMOTO 862,JAPAN
关键词
D O I
10.1016/0040-4039(94)02375-L
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The differentiation between enantiotopic carbonyl groups of cyclic meso-dicarboxylic anhydrides has been attained with excellent diastereofacial selectivity with an isomer ratio above 99 : 1 by treatment with the lithium salts of sterically hindered chiral N-arylsulfonyl-2-aminoalcohols in the presence of hexamethylphosphoric triamide.
引用
收藏
页码:931 / 934
页数:4
相关论文
共 24 条
[1]   NOVEL ROUTE TO SOME BIOLOGICALLY IMPORTANT COMPOUNDS STARTING WITH A COMMON CHIRAL, BICYCLIC, FUSED LACTONE - ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE AND 2 ANTITHROMBOTICS [J].
ARAI, Y ;
KAWANAMI, S ;
KOIZUMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :2969-2975
[2]  
ARAI Y, 1990, J CHEM SOC P1, P1223
[3]   STEREOSELECTIVE SYNTHESIS OF A TRANS-OCTAHYDROINDOLE DERIVATIVE, PRECURSOR OF TRANDOLAPRIL (RU-44 570), AN INHIBITOR OF ANGIOTENSIN CONVERTING ENZYME [J].
BRION, F ;
MARIE, C ;
MACKIEWICZ, P ;
ROUL, JM ;
BUENDIA, J .
TETRAHEDRON LETTERS, 1992, 33 (34) :4889-4892
[4]  
GARY BF, 1993, TETRAHEDRON LETT, V34, P1091
[5]  
GARY BF, 1992, TETRAHEDRON LETT, V32, P4533
[6]   HIGHLY REGIOSELECTIVE RING-OPENING OF ALPHA-SUBSTITUTED CYCLIC ACID ANHYDRIDES CATALYZED BY LIPASE [J].
HIRATAKE, J ;
YAMAMOTO, K ;
YAMAMOTO, Y ;
ODA, J .
TETRAHEDRON LETTERS, 1989, 30 (12) :1555-1556
[7]   ENANTIOTOPIC-GROUP DIFFERENTIATION - CATALYTIC ASYMMETRIC RING-OPENING OF PROCHIRAL CYCLIC ACID ANHYDRIDES WITH METHANOL, USING CINCHONA ALKALOIDS [J].
HIRATAKE, J ;
INAGAKI, M ;
YAMAMOTO, Y ;
ODA, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05) :1053-1058
[8]  
IGNAC JJ, 1982, J AM CHEM SOC, V104, P4659
[9]  
IOANNIS NH, 1993, TETRAHEDRON LETT, V34, P2593
[10]   STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDIN SYNTHONS [J].
JONES, G ;
RAPHAEL, RA ;
WRIGHT, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (14) :1676-1683