Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

Csaba Paizs, Monica Toşa, Viktória Bódai, György Szakács, Ildikó Kmecz, Béla Simándi, Cornelia Majdik, Lajos Novák, Florin Dan Irimie, László Poppe

Research output: Article

34 Citations (Scopus)

Abstract

Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (E≫100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanols (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d.

Original languageEnglish
Pages (from-to)1943-1949
Number of pages7
JournalTetrahedron Asymmetry
Volume14
Issue number13
DOIs
Publication statusPublished - júl. 4 2003

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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