Iterative enolate Claisen rearrangements: Versatile route to optically pure 2,7-nonadiene-5-carboxylic acids

John C. McKew, Mark J. Kurth

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

A short, versatile, and diastereoselective method of preparing 2,7-nonadiene-5-carboxylic acids by an iterative enolate Claisen rearrangement procedure has been developed. Homochiral (E)- and (Z) secondary allylic alcohols 1-4, prepared from (S)-(-)-ethyl lactate, were esterified with acetic acid and enolized, and the resulting silyl ketene acetals were warmed to room temperature to effect [3,3]-sigmatropic rearrangement to 4-hexenoic acids 5-8. Esterification of these acids with alcohols 1-4 followed by a second enolate Claisen rearrangement delivered the targeted 2,7-nonadiene-5-carboxylic acids with high diastereoselectivity. This second [3,3]-sigmatropic rearrangement provides well-placed and potentially synthetically useful functionality and stereochemistry.

Original languageEnglish (US)
Pages (from-to)4589-4595
Number of pages7
JournalJournal of Organic Chemistry
Volume58
Issue number17
StatePublished - 1993

ASJC Scopus subject areas

  • Organic Chemistry

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