Preparation of β-hydroxy-α-phenylthio esters via condensation of aldehydes with α-phenylthio ester enolate anions

Thomas R. Hoye, Mark J. Kurth

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

The lithium enolates of α-phenylthio esters 5 react with aldehydes 6 to give good yields of diastereomeric aldol products 7 and 8 provided that anhydrous zinc chloride is first added to the enolate solution. The threo or erythro nature of several of the aldol products (7 and 8) was determined by transforming them stereospecifically to Z and E olefins 15 through a net trans elimination of the elements of PhSOH. α-(Phenylthio)-γ-butyrolactone (16) also takes part in the aldol reaction.

Original languageEnglish (US)
Pages (from-to)3549-3554
Number of pages6
JournalJournal of Organic Chemistry
Volume45
Issue number18
StatePublished - 1980
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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