Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester

Masayuki Sakuma, Akira Sakakura, Kazuaki Ishihara

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= kfast/k slow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.

Original languageEnglish
Pages (from-to)2838-2841
Number of pages4
JournalOrganic Letters
Volume15
Issue number11
DOIs
Publication statusPublished - Jun 26 2013

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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