Enantioselective dichlorination of allylic alcohols

J Am Chem Soc. 2011 Jun 1;133(21):8134-7. doi: 10.1021/ja202555m. Epub 2011 May 10.

Abstract

The development of an enantioselective allylic alcohol dichlorination catalyzed by dimeric cinchona alkaloid derivatives and employing aryl iododichlorides as chlorine sources is reported. Reaction optimization, exploration of the substrate scope, and a model for stereoinduction are presented.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Allyl Compounds / chemistry*
  • Chlorine / chemistry*
  • Cinchona Alkaloids / chemistry*
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Cinchona Alkaloids
  • Propanols
  • allyl alcohol
  • Chlorine
  • cinnamyl alcohol