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Communication | Special issue | Vol 66, No. 1, 2005, pp.147-151
Published online, 1st November, 2005
DOI: 10.3987/COM-05-S(K)57
Novel Protocol for the Asymmetric Synthesis of 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via Bakers’ Yeast Reduction

Takuzo Komiyama, Yutaka Takaguchi, and Sadao Tsuboi*

*Department of Environmental Chemistry and Materials, Faculty of Environmental Science and Technology, Okayama University, 2-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers’ yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)propionates. Further reduction of a nitro group and cyclization gave the title compound.