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Communication | Special issue | Vol 66, No. 1, 2005, pp.75-80
Published online, 21st October, 2005
DOI: 10.3987/COM-05-S(K)24
■ A Cation-Exchange Resin Promoted Imino Aldol Reaction of Chiral Alkoxyketene Silyl Acetals with α,β-Unsaturated Imines, Leading to a Facile Synthesis of β-Lactams

Makoto Shimizu,* Masanori Tachi, Shiho Fukukshima, and Iwao Hachiya

*Department of Chemistry for Materials, Faculty of Engineering, Mie University, 1515 Uehama-cho, Tsu, Mie 514-5807, Japan

Abstract

Imino aldol reaction of chiral ketene silyl acetals derived from 3-hydroxybutanoates with α,β-unsaturated imines proceeds smoothly to give β-amino esters in good yields with high syn-selectivity under the influence of a cation-exchange resin. Subsequent treatment with tert-butylmagnesium chloride gave β-lactams in a highly stereoselective manner.