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Note | Special issue | Vol 66, No. 1, 2005, pp.603-610
Published online, 18th October, 2005
DOI: 10.3987/COM-05-S(K)40
Asymmetric Mannich-Type Addition of Lithium Glycolates to Imines Producing 3-Hydroxy-4-phenylazetidin-2-ones

Hiroki Fujieda, Seiji Hata, Ken-ichi Yamada, and Kiyoshi Tomioka*

*Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

The external chiral ligand-controlled asymmetric Mannich-type reaction of a binary- or ternary-complexed lithium ester enolate of protected glycolates with benzaldehyde imines gave the corresponding 3-trialkylsilyloxy-4-phenylazetidin-2-ones, applicable as a synthetic intermediate of C13 side chain of taxan anticancer drugs, in moderate enantioselectivity.