Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles

Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8661-4. doi: 10.1002/anie.201204469. Epub 2012 Jul 23.

Abstract

Reduction, please! The title reaction affords α-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Ketones / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Ketones
  • Nitriles
  • Titanium