STEREOSELECTIVE SYNTHESIS OF ENANTIOPURE 4,5-DISUBSTITUTED PYRROLIDIN-2-ONES BY CONSECUTIVE CUPRATE ADDITION AND N-ACYLIMINIUM COUPLING

被引：35

作者：

KOOT, WJ ^{[1
]}

HIEMSTRA, H ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)74791-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiopure gamma-lactam (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one (1), prepared from (S)-malic acid, undergoes cuprate addition at C4 with complete trans-stereoselectivity. The products react with pi-nucleophiles in the presence of Lewis acid at C5 to provide enantiopure 4,5-disubstituted pyrrolidin-2-ones.

引用

页码：7969 / 7972

页数：4

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