Reactivity of chiral α-amidoalkylphenyl sulfones with stabilized carbanions.: Stereoselective synthesis of optically active 1-aminopyrrolizidine

被引：32

作者：

Giri, N ^{[1
]}

Petrini, M ^{[1
]}

Profeta, R ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 21期

关键词：

D O I：

10.1021/jo048882y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metal enolates and functionalized allylzinc reagents react with optically active alpha-amidoalkylphenyl sulfones to give N-carbamoylamino derivatives with variable levels of anti diastereoselectivity. Zinc enolates provide comparable results with respect to lithium enolates in terms of diastereoselectivity but afford beta-amino ester derivatives in lower yield. The synthetic utility of the obtained chiral N-carbamoylamino esters is demonstrated by the first enantioselective synthesis of (-)-1-aminopyrrolizidine a central intermediate for the preparation of various biologically active substances.

引用

页码：7303 / 7308

页数：6

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