Novel Carbonyl Bromoallylation/Heck Reaction Sequence. Stereocontrolled Access to Bicyclic β-Lactams

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...

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Veröffentlicht in:	Journal of organic chemistry 2005-04, Vol.70 (7), p.2713-2719
Hauptverfasser:	Alcaide, Benito, Almendros, Pedro, Rodríguez-Acebes, Raquel
Format:	Artikel
Sprache:	eng
Schlagworte:	beta-Lactams - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Organic chemistry Preparations and properties Spectrophotometry, Infrared
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	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 β-lactams of nonconventional structure via Heck cyclization.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0478306