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
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
收藏
页码:937 / 940
页数:4
相关论文
共 14 条