Behaviour of dioxolanones as chiral acyl anion equivalents

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

The 1,3-dioxolan-4-ones readily derived from alpha-hydroxy acids act as convenient acyl anion equivalents by deprotonation - alkylation Followed by flash vacuum pyrolysis. Conjugate addition of their anions to ethyl crotonate similarly gives beta-methyl-gamma-oxo esters and by using chiral dioxolanones these can be obtained in up to 86% e.e.

Original languageEnglish
Pages (from-to)102-104
Number of pages4
JournalSynlett
Publication statusPublished - Jan 1998

Keywords

  • chiral acyl anion equivalents
  • 1,3-dioxolan-4-ones
  • flash vacuum pyrolysis
  • asymmetric synthesis
  • ASYMMETRIC NUCLEOPHILIC ACYLATION
  • FORMALDEHYDE SAMP-HYDRAZONE
  • ENANTIOSELECTIVE SYNTHESIS
  • MICHAEL ADDITION
  • AMINO NITRILES
  • ALKYLATION
  • NITROOLEFINS

Fingerprint

Dive into the research topics of 'Behaviour of dioxolanones as chiral acyl anion equivalents'. Together they form a unique fingerprint.

Cite this