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 journalArticle

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 languageEnglish
Pages (from-to)147-151
Number of pages5
JournalHeterocycles
Volume66
Issue number1
DOIs
Publication statusPublished - Dec 31 2005

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Propionates
Cyclization
Yeast
Saccharomyces cerevisiae
Sodium
Condensation reactions
Substitution reactions
4-anisaldehyde

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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. / Komiyama, Takuzo; Takaguchi, Yutaka; Tsuboi, Sadao.

In: Heterocycles, Vol. 66, No. 1, 31.12.2005, p. 147-151.

Research output: Contribution to journalArticle

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