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Paper | Special issue | Vol 52, No. 1, 2000, pp.227-236
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S14
Highly Diastereoselective Reduction of γ-Keto Amides: Diastereoselective Synthesis of γ-Butyrolactones with Contiguous Chiral Centers

Masami Satoh, Sakurako Washida, Sawako Takeuchi, and Morio Asaoka*

*Department of Chemical and Biological Sciences, Faculty of Science, Japan Women's University, 2-8-1 Mejirodai, Bunkyoku, Tokyo 112-0015, Japan

Abstract

Diastereoselective reduction of γ-keto amides, which were easily prepared by the reaction of a zinc homoenolate of butanamide with acid chlorides in the presence of Pd(0) catalyst, was achieved. Cyclization of the products, γ-hydroxy amides, under various conditions gave α,β-disubstituted and α,β,γ-trisubstituted γ-butyrolatones with high diastereoisomeric purities.