Chemoenzymatic one-pot synthesis in an aqueous medium: combination of metal-catalysed allylic alcohol isomerisation-asymmetric bioamination

Chem Commun (Camb). 2015 Jul 11;51(54):10937-40. doi: 10.1039/c5cc03298a.

Abstract

The ruthenium-catalysed isomerisation of allylic alcohols was coupled, for the first time, with asymmetric bioamination in a one-pot process in an aqueous medium. In the cases involving prochiral ketones, the ω-TA exhibited excellent enantioselectivity, identical to that observed in the single step. As a result, amines were obtained from allylic alcohols with high overall yields and excellent enantiomeric excesses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Catalysis
  • Ketones / chemistry
  • Propanols / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism
  • Water / chemistry

Substances

  • Ketones
  • Propanols
  • Water
  • allyl alcohol
  • Ruthenium