Stereoselective Entry to Bicyclic β-Lactams via Free Radical Cyclization of 2-Azetidinone-Tethered Bromohomoallylic Alcohols

Benito Alcaide; Pedro Almendros; Raquel Rodríguez-Acebes

doi:10.1055/s-2005-869985

PAPER

Stereoselective Entry to Bicyclic β-Lactams via Free Radical Cyclization of 2-Azetidinone-Tethered Bromohomoallylic Alcohols

Benito Alcaide*^a, Pedro Almendros*^b, Raquel Rodríguez-Acebes^a
^a Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040-Madrid, Spain
Fax: +34(91)3944103; e-Mail: alcaideb@quim.ucm.es;
^b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain
Fax: +34(91)564853; e-Mail: iqoa392@iqog.csic.es;

Abstract

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Abstract

Triphenyltin hydride-promoted reaction of β-lactam-tethered bromodienes gave six-, seven-, or eight-membered bicyclic ring structures through intramolecular free radical cyclization. The cyclization precursors were synthesized by stereoselective tin-mediated carbonyl bromoallylation of 4-oxoazetidine-2-carbaldehydes in an aqueous environment.

Key words

carbonyl additions - cyclizations - lactams - radical reactions - tin

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References

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