STEREOSELECTIVE ADDITION OF GRIGNARD-DERIVED ORGANOCOPPER REAGENTS TO N-ACYLIMINIUM IONS - SYNTHESIS OF ENANTIOPURE 5-SUBSTITUTED AND 4,5-SUBSTITUTED PROLINATES

被引：76

作者：

COLLADO, I ^{[1
]}

EZQUERRA, J ^{[1
]}

PEDREGAL, C ^{[1
]}

机构：

[1] CTR INVEST LILLY SA,E-28130 VALDEOLMOS,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 16期

关键词：

D O I：

10.1021/jo00121a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents. The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates. The stereochemistry is controlled by the formation of a RCu-pi complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.

引用

页码：5011 / 5015

页数：5

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