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Paper | Special issue | Vol 40, No. 2, 1995, pp.691-716
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S57
Preparation of beta-Lactams from beta-Hydroxy Amides, and Annulation of N-Malonyl beta-Lactams by Manganese(III) Acetate-promoted Free Radical Cyclization and by Aldol Cyclization

Peter J. Crocker, Ulrika Karlsson-Andreasson, Bruce T. Lotz, and Marvin J. Miller

*Department of Chemistry and Biochemistry, College of Science, University of Notre Dame, Notre Dame, IN 46556, U.S.A.

Abstract

β-Lactams are formed from β-hydroxy amides by base-promoted cyclization of the β-methylsulfonoxyamide. In the system studied, this amide-based mesylate cyclization proceeded in high yields, whereas the analogous β-chloroamide afforded only the α,β-unsaturated amide. Also, two new methods of synthesizing carbacephams by annulation of malonate-substituted β-lactams were demonstrated. The first was a manganese(III) acetate-promoted oxidative free radical cyclization. The second was a spontaneous aldol cyclization of an intermediate aldehyde generated by ozonolysis of an alkene.