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Communication | Special issue | Vol 52, No. 3, 2000, pp.1001-1004
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S95
Stereoselective Synthesis of Optically Active β-Lactams by the Reaction of Chiral Imines Derived from erythro-2-Amino-1,2-diphenylethanol with Ester Enolates

Yukihiko Hashimoto,* Tsuneo Ogasawara, Minoru Hayashi, and Kazuhiko Saigo*

*Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656, Japan

Abstract

Chiral imines, derived from (1S,2R)-2-methoxy-1,2-diphenylethyl-amine and aromatic aldehydes, reacted with ester enolates prepared from ketene silyl acetals and methyllithium to give β-lactams in good yields with high diastereoselectivity. This method provides a useful and simple route for the construction of optically active β-lactam skeletons.