Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Brønsted acid

Takuto Yamanaka, Azusa Kondoh, Masahiro Terada

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The kinetic resolution of racemic secondary alcohols is a fundamental method for obtaining enantiomerically enriched alcohols. Compared to esterification, which is a well-established method for this purpose, kinetic resolution through enantioselective intermolecular acetalization has not been reported to date despite the fact that the formation of acetals is widely adopted to protect hydroxy groups. By taking advantage of the thermodynamics of acetalization by the addition of alcohols to enol ethers, a highly efficient kinetic resolution of racemic amino alcohols was achieved for the first time and in a practical manner using a chiral phosphoric acid catalyst.

Original languageEnglish
Pages (from-to)1048-1051
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number3
DOIs
Publication statusPublished - 2015 Jan 28

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Brønsted acid'. Together they form a unique fingerprint.

  • Cite this