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Synthesis 2005(14): 2335-2340
DOI: 10.1055/s-2005-869985
DOI: 10.1055/s-2005-869985
PAPER
© Georg Thieme Verlag Stuttgart · New YorkStereoselective Entry to Bicyclic β-Lactams via Free Radical Cyclization of 2-Azetidinone-Tethered Bromohomoallylic Alcohols
Further Information
Received
16 February 2005
Publication Date:
27 June 2005 (online)
Publication History
Publication Date:
27 June 2005 (online)

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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