CONFORMATIONALLY RIGID CHIRAL [4+2]CYCLOADDUCT-BASED 2-OXAZOLIDINONES AS NEW AUXILIARIES

被引:37
作者
MATSUNAGA, H
KIMURA, K
ISHIZUKA, T
HARATAKE, M
KUNIEDA, T
机构
[1] KUMAMOTO UNIV,FAC PHARMACEUT SCI,KUMAMOTO 862,JAPAN
[2] YOSHITOMI RES LABS,YOSHITOMI,FUKUOKA 871,JAPAN
关键词
D O I
10.1016/0040-4039(91)80573-O
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Newly introduced enantiomerically pure [4 + 2]cycloadduct-based 2-oxazolidinones which are conformationally fixed by bicyclo[2.2.2] and [2.2.1] ring systems, serve well as exellent chiral auxiliaries in the Evans' asymmetric strategy.
引用
收藏
页码:7715 / 7718
页数:4
相关论文
共 16 条
[1]  
BORNER MR, 1991, J AM CHEM SOC, V113, P1299
[2]   CLEAVAGE OF N-ACYL OXAZOLIDONES [J].
DAMON, RE ;
COPPOLA, GM .
TETRAHEDRON LETTERS, 1990, 31 (20) :2849-2852
[3]  
DEYRUP JA, 1977, TETRAHEDRON LETT, P3115
[4]  
Evans D. A., 1982, ALDRICHIM ACTA, V15, P23
[5]   NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].
EVANS, DA ;
URPI, F ;
SOMERS, TC ;
CLARK, JS ;
BILODEAU, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216
[6]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[7]   OPTICALLY-ACTIVE ALPHA-ALKYLSUCCINATES FROM THE STEREOSELECTIVE ALKYLATION OF CHIRAL IMIDE ENOLATES [J].
FADEL, A ;
SALAUN, J .
TETRAHEDRON LETTERS, 1988, 29 (48) :6257-6260
[8]   ACYCLIC STEREOSELECTION IN THE ALKYLATION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS - A SELF-IMMOLATIVE CHIRALITY TRANSFER PROCESS FOR THE SYNTHESIS OF PRIMARY AMINES [J].
GAWLEY, RE ;
REIN, K ;
CHEMBURKAR, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3002-3004
[9]   NEW CAMPHOR-DERIVED AUXILIARIES IN METHOXYSELENYLATION AND METHOXYBROMINATION WITH OPPOSITE DIASTEREOFACIAL SELECTIVITY - PREPARATION OF BETA-AMINO ALCOHOL CHIRAL SYNTHONS [J].
ISHIZUKA, T ;
ISHIBUCHI, S ;
KUNIEDA, T .
TETRAHEDRON LETTERS, 1989, 30 (26) :3449-3452
[10]  
ISHIZUKA T, 1990, CHEM PHARM BULL, V38, P1717