Radical cyclization of chiral N-(1-cycloalken-1-yl)-alpha-haloacetamides: Synthesis of optically active bicyclic pyrrolidinones

被引：43

作者：

Ishibashi, H ^{[1
]}

Fuke, Y ^{[1
]}

Yamashita, T ^{[1
]}

Ikeda, M ^{[1
]}

机构：

[1] KYOTO PHARMACEUT UNIV,YAMASHIMA KU,KYOTO 607,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 09期

关键词：

D O I：

10.1016/0957-4166(96)00326-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric induction in the 5-endo-trig radical cyclization of N-(1-cycloallren-1-yl> a-haloacetamides has been examined. alpha-Iodo amide 7 bearing an (S)-1-(1-naphthyl)ethyl group on the nitrogen afforded a 92:8 mixture of bicyclic lactams 9a,b, which was transformed into (3aR,7aR)-octahydroindol-2-one 10a in 77% ee. alpha-Bromo amide 11 bearing an N-(R)-1-phenethyl group provided a 61:39 mixture of 13a,b. The major product 13a was then transformed into enantiomerically pure (1S,5S)-2-azabicyclo[3.3.0]octan-3-one 15. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：2531 / 2538

页数：8

共 46 条

[1] SOME DIASTEREOSELECTIVE RADICAL REACTIONS OF SUBSTITUTED 1,3-DIOXOLAN-4-ONES [J].