Catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones

Org Lett. 2008 Sep 18;10(18):4041-4. doi: 10.1021/ol801574m. Epub 2008 Aug 21.

Abstract

The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me2Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Catalysis
  • Ketones / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Alcohols
  • Ketones