Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction

Kazuaki Ishihara, Yuji Kosugi, Shuhei Umemura, Akira Sakakura

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

(Chemical Equation Presented) The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Brønsted base such as O-protected α-hydroxy carboxylic acids and N-protected α-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S(kfast/kslow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.

Original languageEnglish
Pages (from-to)3191-3194
Number of pages4
JournalOrganic Letters
Volume10
Issue number15
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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