Highly stereoselective aldol reaction for the synthesis of γ-lactones starting from tartaric acid

M. Teresa Barros, Anthony J. Burke, Ji Dong Lou, Christopher D. Maycock, Jorge R. Wahnon

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A simple stereoselective process for the synthesis of highly substituted γ-lactones was developed based on aldol reactions between the enolate of dioxanes derived from tartaric acid and aldehydes. A range of aromatic and aliphatic aldehydes were reacted, in most cases achieving good yields and stereoselectivity. The limitations of this reaction were identified and a transition state is proposed.

Original languageEnglish
Pages (from-to)7847-7850
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number23
DOIs
Publication statusPublished - 12 Nov 2004

Keywords

  • Enolates
  • Lactones
  • Aldehydes
  • Aldol reactions
  • Cyclization

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