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
[11]  
JOSEPH C, 1994, TETRAHEDRON LETT, V35, P1515
[12]  
JOSEPH CF, 1993, TETRAHEDRON LETT, V34, P257
[13]  
KAR PL, 1985, J AM CHEM SOC, V107, P2521
[14]   EXTREMELY POWERFUL CHIRAL AUXILIARIES - ENANTIOMERIC [4+2] CYCLOADDUCTS OF 2-OXAZOLONE AND 9,10-DIMETHYLANTHRACENE [J].
KIMURA, K ;
MURATA, K ;
OTSUKA, K ;
ISHIZUKA, T ;
HARATAKE, M ;
KUNIEDA, T .
TETRAHEDRON LETTERS, 1992, 33 (31) :4461-4464
[15]  
LIEB F, 1987, LIEBIGS ANN CHEM, P607
[16]   HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-CYCLIC-1,2-DICARBOXIMIDES - ASYMMETRIC-SYNTHESIS OF BICYCLIC 2-PYRROLIDINONE AND ITS 5-HYDROXY CONGENER [J].
MATSUKI, K ;
INOUE, H ;
ISHIDA, A ;
TAKEDA, M ;
NAKAGAWA, M ;
HINO, T .
HETEROCYCLES, 1993, 36 (05) :937-940
[17]   HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-1,2-DICARBOXYLIC ANHYDRIDES [J].
MATSUKI, K ;
INOUE, H ;
TAKEDA, M .
TETRAHEDRON LETTERS, 1993, 34 (07) :1167-1170
[18]   CONFORMATIONALLY RIGID CHIRAL [4+2]CYCLOADDUCT-BASED 2-OXAZOLIDINONES AS NEW AUXILIARIES [J].
MATSUNAGA, H ;
KIMURA, K ;
ISHIZUKA, T ;
HARATAKE, M ;
KUNIEDA, T .
TETRAHEDRON LETTERS, 1991, 32 (52) :7715-7718
[19]  
Ohno M., 1989, ORGANIC REACTIONS, V37, P1
[20]   HIGHLY EFFECTIVE AND PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF HALF-ESTERS OF BICYCLO[2.2.1]HEPTANEDICARBOXYLIC ACID [J].
OHTANI, M ;
MATSUURA, T ;
WATANABE, F ;
NARISADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4120-4123