Synthesis of chiral 3-alkyl-3,4-dihydroisocoumarins by dynamic kinetic resolutions catalyzed by a Baeyer-Villiger monooxygenase

J Org Chem. 2010 Mar 19;75(6):2073-6. doi: 10.1021/jo902519j.

Abstract

Baeyer-Villiger monooxygenases have been tested in the oxidation of racemic benzofused ketones. When employing a single mutant of phenylacetone monooxygenase (M446G PAMO) under the proper reaction conditions, it was possible to achieve 3-substituted 3,4-dihydroisocoumarins with high yields and optical purities through regioselective dynamic kinetic resolution processes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Kinetics
  • Mixed Function Oxygenases / chemistry*
  • Mixed Function Oxygenases / genetics
  • Models, Molecular
  • Molecular Structure
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Stereoisomerism

Substances

  • Coumarins
  • Recombinant Proteins
  • Mixed Function Oxygenases