HIGHLY DIASTEREOSELECTIVE MICHAEL ADDITION OF LITHIATED CAMPHOR IMINES OF GLYCINE ESTERS TO ALPHA,BETA-UNSATURATED ESTERS - SYNTHESIS OF OPTICALLY PURE 5-OXO-2,4-PYRROLIDINEDICARBOXYLATES OF UNNATURAL STEREOCHEMISTRY

被引：64

作者：

KANEMASA, S ^{[1
]}

TATSUKAWA, A ^{[1
]}

WADA, E ^{[1
]}

机构：

[1] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 08期

关键词：

D O I：

10.1021/jo00008a052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithium enolates of camphor imines of glycine esters underwent highly diastereoselective Michael additions to alpha,beta-unsaturated esters. The tightly chelated structure of the Z,E enolates and the selective approach of the alpha,beta-unsaturated esters to the re face of the enolates were responsible for the high diastereoselectivity observed. The use of alkylidenemalonate acceptors led to the diastereospecific formation of Michael adducts. Removal of the camphor auxiliary of the adducts and concomitant cyclization led to optically pure enantiomeric 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry.

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页码：2875 / 2883

页数：9

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