Organocatalytic asymmetric vinylogous addition to quinones - formation of optically active alpha-aryl ketones

Chem Commun (Camb). 2008 Feb 7:(5):632-4. doi: 10.1039/b716485h. Epub 2007 Nov 28.

Abstract

The first organocatalytic addition of dicyanoalkylidenes to quinones catalyzed by Cinchona alkaloids leading to formation of 1,4-diketone derivatives with high diastereomeric ratios (up to >98 : <2 dr) and enantioselectivities (up to 99% ee) has been developed; the optically active compounds obtained are useful for a number of transformations, e.g. the synthesis of optically active alpha-aryl ketones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Conformation
  • Nitriles / chemistry*
  • Quinones / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Cinchona Alkaloids
  • Ketones
  • Nitriles
  • Quinones