Asymmetric syntheses of fused bicyclic compounds by conjugate additions of allylic organolithium species to activated olefins and subsequent cyclizations

被引：31

作者：

Lim, SH ^{[1
]}

Curtis, MD ^{[1
]}

Beak, P ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 05期

关键词：

D O I：

10.1021/ol007012+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of the configurationally stable organolithium species produced by enantioselective deprotonation of N-BOC-N-(p-methoxyphenyl) allylamines to alpha,beta -unsaturated carbonyl compounds affords 1,4-addition products in good yields with high diastereomeric and enantiomeric ratios. Further transformations of these compounds provide [3.3.0]-, [4.3.0]-, [5.3.0]-, and [5.4.0]-carbocycles and heterscycles with high stereoselectivities.

引用

页码：711 / 714

页数：4

共 16 条

[1] An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase [J].