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Communication | Special issue | Vol 49, No. 1, 1998, pp.97-100
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S44
Organic Reactions in Water: Indium Mediated Synthesis of α-Alkylidene-β-lactams

Muthusamy Jayaraman, Maria T. Batista, Maghar S. Manhas, and Ajay K. Bose*

*George Barasch Bioorganic Laboratory, Department of Chemistry and Chemical Biology, Stevens Institute of Technology, Hoboken, NJ 07030, U. S. A.

Abstract

Indium mediated Barbier type addition of allyl bromides to azetidine-2,3-diones (1) in aqueous media provided two homoallylic alcohols (for example, 2 and 3) which on mesylation followed by elimination in the presence of DBU gave a mixture of E and Z isomers of α-alkylidene-β-lactams (4 and 5) in excellent yield. These highly substituted β-lactams are versatile synthons for a variety of structures.