Chemoenzymatic dynamic kinetic resolution of axially chiral allenes

Chemistry. 2010 Apr 19;16(15):4447-51. doi: 10.1002/chem.201000301. Epub 2010 Mar 22.

Abstract

At the palladium: Dimeric palladium bromide complexes bearing monodentate N-heterocyclic carbene ligands have been identified as efficient catalysts for the chemoselective racemization of axially chiral allenyl alcohols. In combination with porcine pancreatic lipase as biocatalyst, a dynamic kinetic resolution has been developed, giving access to optically active allenes in good yield and high enantiomeric purity (see scheme).

Keywords: allenes; biocatalysis; dynamic kinetic resolution; palladium; racemization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Animals
  • Butyrates / chemical synthesis*
  • Butyrates / chemistry
  • Catalysis
  • Kinetics
  • Ligands
  • Lipase / metabolism*
  • Molecular Structure
  • Palladium / chemistry*
  • Pancreas / enzymology*
  • Stereoisomerism
  • Swine / metabolism

Substances

  • Alcohols
  • Alkadienes
  • Butyrates
  • Ligands
  • propadiene
  • Palladium
  • Lipase