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; Sadao Tsuboi

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, Sadao Tsuboi

Research output: Contribution to journal › Article

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	147-151
Number of pages	5
Journal	Heterocycles
Volume	66
Issue number	1
DOIs	https://doi.org/10.3987/COM-05-S(K)57
Publication status	Published - Dec 31 2005

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Organic Chemistry

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Komiyama, T., Takaguchi, Y., & Tsuboi, S. (2005). 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. Heterocycles, 66(1), 147-151. https://doi.org/10.3987/COM-05-S(K)57

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10.3987/COM-05-S(K)57