Intermolecular dynamic kinetic resolution cooperatively catalyzed by an N-heterocyclic carbene and a Lewis acid

Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1629-33. doi: 10.1002/anie.201410030. Epub 2014 Nov 28.

Abstract

The ubiquitous structure of δ-lactones makes the development of new methods for their enantioselective and stereoselective synthesis an important ongoing challenge. The intermolecular dynamic kinetic resolution (DKR) of β-halo-α-ketoesters cooperatively catalyzed by an N-heterocyclic carbene and a Lewis acid generates two contiguous stereocenters with remarkable diastereoselectivity through an oxidation/lactonization sequence.

Keywords: N-heterocyclic carbene; annulation; dynamic kinetic resolution; lactones; oxidative addition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Kinetics
  • Lactones / chemistry
  • Lewis Acids / chemistry*
  • Mesylates / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Lactones
  • Lewis Acids
  • Mesylates
  • carbene
  • trifluoromethanesulfonic acid
  • Methane