Lipase-catalyzed highly enantioselective kinetic resolution of boron-containing chiral alcohols

Org Lett. 2009 Jul 16;11(14):3052-5. doi: 10.1021/ol901091f.

Abstract

The first application of enzymes as catalysts to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses (up to >99%) of both remaining substrates and acetylated product were obtained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Boron Compounds / chemistry*
  • Candida / enzymology*
  • Catalysis
  • Lipase / metabolism*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alcohols
  • Boron Compounds
  • Lipase