ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION OF N-ALLYLIC- AND N-HOMOALLYLIC DIAZOACETAMIDES CATALYZED BY CHIRAL DIRHODIUM(II) CATALYSTS

被引：25

作者：

DOYLE, MP

EISMONT, MY

PROTOPOPOVA, MN

KWAN, MMY

机构：

[1] Department of Chemistry, Trinity University, San Antonio

来源：

TETRAHEDRON | 1994年 / 50卷 / 06期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4020(01)80842-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diazodecomposition of N-(tert-butyl)-N-(3-buten-1-yl)diazoacetamides catalyzed by dirhodium(II) tetrakis[methyl 2-pyrrolidone-5(S)-carboxylate], Rh-2(5S-MEPY)(4), and tetrakis[methyl 2-oxazolidinone-4(S)-carboxylate], Rh-2(4S-MEOX)(4), forms products from intramolecular cyclopropanation in good yields with enantiomeric excesses ranging from 60-90%. Intramolecular cyclopropanation with N,N-diallyldiazoacetamide (72% ee) is competitive with intramolecular [3+2] dipolar cycloaddition.

引用

收藏

页码：1665 / 1674

页数：10

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