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

28 Citations (Scopus)

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

Fingerprint

Aldehydes
Anions
Condensation
Esters
Alkenes
Lithium
3-hydroxybutanal
zinc chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of β-hydroxy-α-phenylthio esters via condensation of aldehydes with α-phenylthio ester enolate anions. / Hoye, Thomas R.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 45, No. 18, 1980, p. 3549-3554.

Research output: Contribution to journalArticle

@article{6877598f89694acd8087aaf7930de712,
title = "Preparation of β-hydroxy-α-phenylthio esters via condensation of aldehydes with α-phenylthio ester enolate anions",
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.",
author = "Hoye, {Thomas R.} and Kurth, {Mark J.}",
year = "1980",
language = "English (US)",
volume = "45",
pages = "3549--3554",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - Preparation of β-hydroxy-α-phenylthio esters via condensation of aldehydes with α-phenylthio ester enolate anions

AU - Hoye, Thomas R.

AU - Kurth, Mark J.

PY - 1980

Y1 - 1980

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0000339002&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000339002&partnerID=8YFLogxK

M3 - Article

VL - 45

SP - 3549

EP - 3554

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -