Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

Julia A. Kalow, Abigail Gutmann Doyle

Research output: Contribution to journalArticle

166 Scopus citations

Abstract

(Figure Presented) An enantioselective method for the synthesis of β-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with krel values as high as 300.

Original languageEnglish (US)
Pages (from-to)3268-3269
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number10
DOIs
StatePublished - Mar 17 2010

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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