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
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.
引用
收藏
页码:2713 / 2719
页数:7
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