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

被引：12
|
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 / 15期
关键词：
D O I：
10.1016/S0040-4020(01)89383-2
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：4519 / 4528
页数：10
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