Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions

Mark J. Kurth; Thomas R Hoye

doi:10.1021/jo01306a002

Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions

Mark J. Kurth, Thomas R Hoye

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

The lithium enolates of -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 language	English (US)
Pages (from-to)	3549-3554
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	45
Issue number	18
DOIs	https://doi.org/10.1021/jo01306a002
State	Published - Aug 1980

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title = "Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions",

abstract = "The lithium enolates of -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.",

author = "Kurth, {Mark J.} and Hoye, {Thomas R}",

year = "1980",

month = aug,

doi = "10.1021/jo01306a002",

language = "English (US)",

volume = "45",

pages = "3549--3554",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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AB - The lithium enolates of -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.

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Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions

Abstract

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