Stereochemically controlled asymmetric 1,2-reduction of enones mediated by a chiral sulfoxide moiety and a lanthanum(III) ion

J Org Chem. 2011 May 20;76(10):3922-36. doi: 10.1021/jo200373a. Epub 2011 Apr 28.

Abstract

Enantiomerically pure (Z)-β-sulfinyl allylic alcohols of either handedness can be readily prepared from (Z)-β-sulfinyl enones using NaBH(4) or DIBAL reductants in the presence of LaCl(3) as a chelating agent. A chiral sulfoxide auxiliary induces the remote 1,2-asymmetric reduction (1,4-induction) to afford various chiral allylic alcohols in high yields with excellent stereoselectivities (up to 100% de).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Ketones / chemistry*
  • Lanthanum / chemistry*
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Propanols / chemistry
  • Stereoisomerism
  • Substrate Specificity
  • Sulfoxides / chemistry*

Substances

  • Alkenes
  • Ketones
  • Organometallic Compounds
  • Propanols
  • Sulfoxides
  • allyl alcohol
  • Lanthanum