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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.


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.