Remote stereocontrol by sulfinyl groups: reduction of delta-ketosulfoxides

J Org Chem. 2005 Mar 4;70(5):1796-801. doi: 10.1021/jo047999j.

Abstract

The reduction of delta-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)3 or L-Selectride as the reducing agents provides delta-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Conformation
  • Oxidation-Reduction
  • Stereoisomerism
  • Sulfoxides / chemical synthesis*
  • Sulfoxides / chemistry
  • Sulfur Compounds / chemistry*

Substances

  • Ketones
  • Sulfoxides
  • Sulfur Compounds