Reduction of oximes of. ALPHA.-substituted. BETA.-ketoesters with sodium cyanoborohydride: Stereoselective synthesis of 3, 4-cis-substituted azetidin-2-ones.

T Chiba, T Ishizawa, J Sakaki, C Kaneko

Index: Chiba; Ishizawa; Sakaki; Kaneko Chemical and Pharmaceutical Bulletin, 1987 ,  vol. 35,  # 11  p. 4672-4675

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Citation Number: 10

Abstract

erythro-3-Hydroxyamino-2-alkylbutanoate and its derivatives were prepared stereoselectively by reduction of the oximes of the corresponding β-ketoesters with sodium cyanoborohydride in acidic media. Cyclization of the β-amino acids obtained by reduction and successive hydrolysis gave 3, 4-cis-substituted azetidin-2-ones.