Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates

Eugene A Mash, James A. Fryling

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A concise approach for the rapid synthesis of enantiomerically pure α-alkylated derivatives of lactate esters and of other enantiomerically pure α-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other α-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.

Original languageEnglish (US)
Pages (from-to)1094-1098
Number of pages5
JournalJournal of Organic Chemistry
Volume56
Issue number3
StatePublished - 1991

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Acetals
Alkylation
Esters
Lactates
Ethers
Enantiomers
Lithium
Lactic Acid
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "A concise approach for the rapid synthesis of enantiomerically pure α-alkylated derivatives of lactate esters and of other enantiomerically pure α-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other α-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.",
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