HIGHLY DIASTEREOSELECTIVE FORMATION OF SUBSTITUTED INDOLIZIDINES AND QUINOLIZIDINES BY RADICAL CYCLIZATION

被引：65

作者：

BECKWITH, ALJ

JOSEPH, SP

MAYADUNNE, RTA

机构：

[1] Research School of Chemistry, Australian National University, Canberra

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Substituted 2,3-dihydro-4-pyridinones (eg., 1a) bearing an (omega-bromoacyl)-, (o-bromoaroyl)-, or (o-bromophenyl)aeetyl group on nitrogen, when treated with tributylstannane, undergo highly diastereoselective cyclization by intramolecular homolytic addition anti to the substituent at C-2; molecular mechanics calculation support the view that the diastereoselectivity arises from the nonbonded interaction between the substituent and the amide carbonyl group.

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页码：4198 / 4199

页数：2

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