Novel carbonyl bromoallylation/Heck reaction sequence.: Stereocontrolled access to bicyclic β-lactams

被引：35

作者：

Alcaide, B

Almendros, P

Rodríguez-Acebes, R

机构：

[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[2] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 07期

关键词：

D O I：

10.1021/jo0478306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2,3-dibromopropene with racemic as well as enantiopure 4-oxoazetidine-2-carbaldehydes 1 in aqueous media was promoted by tin in the presence of several additives to afford the corresponding bromohomoallyl alcohols 2 in high diastereoselectivities. However, indium or zinc were unable to promote the bromoallylation reaction of aldehydes 1 under similar Barbier-type conditions. Vinyl bromides 2 bearing an extra alkene tether were used for the preparation of differently sized, fused bicyclic beta-lactams of nonconventional structure via Heck cyclization.

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页码：2713 / 2719

页数：7

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