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 Scopus citations

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 frontaiin from (S)-(-)-methyl lactate.

Original languageEnglish (US)
Pages (from-to)1094-1098
Number of pages5
JournalJournal of Organic Chemistry
Volume56
Issue number3
DOIs
StatePublished - Feb 1 1991

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantiomerically Pure Acetals in Organic Synthesis. 2. Diastereoselective Alkylation of Enantiomeric Lithio Alkyl Lactyl Tetrahydropyranosides and Related Enolates'. Together they form a unique fingerprint.

  • Cite this