REDUCTION OF OXIMES OF α-SUBSTITUTED β-KETOESTERS WITH SODIUM CYANOBOROHYDRIDE : STEREOSELECTIVE SYNTHESIS OF 3, 4-CIS-SUBSTITUTED AZETIDIN-2-ONES

Takuo Chiba; Takenori Ishizawa; Jun-ichi Sakaki; Chikara Kaneko

doi:10.1248/cpb.35.4672

Takuo Chiba, Takenori Ishizawa, Jun-ichi Sakaki, Chikara Kaneko

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Keywords: 3, 4-cis-substituted azetidin-2-one, erythro-β-amino acid, β-hydroxyiminoester, diastereoselective reduction, sodium cyanoborohydride, diastereofacial selectivity

JOURNAL FREE ACCESS

1987 Volume 35 Issue 11 Pages 4672-4675

DOI https://doi.org/10.1248/cpb.35.4672

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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.

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