HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-CYCLIC-1,2-DICARBOXIMIDES - ASYMMETRIC-SYNTHESIS OF BICYCLIC 2-PYRROLIDINONE AND ITS 5-HYDROXY CONGENER

被引：20

作者：

MATSUKI, K ^{[1
]}

INOUE, H ^{[1
]}

ISHIDA, A ^{[1
]}

TAKEDA, M ^{[1
]}

NAKAGAWA, M ^{[1
]}

HINO, T ^{[1
]}

机构：

[1] CHIBA UNIV,FAC PHARMACEUT SCI,INAGE KU,CHIBA 263,JAPAN

来源：

HETEROCYCLES | 1993年 / 36卷 / 05期

关键词：

D O I：

10.3987/COM-92-6307

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic 5-hydroxy-2-pyrrolidinones (2a - f) were synthesized with high enantioselectivity by the reduction of meso underbar-cyclic- 1,2-dicarboximides (1a - f) with lithium aluminum hydride (LiAlH4)- methanol (MeOH)- 1,1'-bi-2-naphthol complex (BINAL-H). Treatment of 2a - f with triethylsilane (Et3SiH) and trifluoroacetic acid(CF3CO2H) gave optically active 2-pyrrolidinones (3a - f) in quantitative yields. For the absolute configuration correlation, 2a - d were converted into known lactones (4a - d).

引用

页码：937 / 940

页数：4

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