Brønsted acid catalyzed asymmetric reduction of ketones and acyl silanes using chiral anti-pentane-2,4-diol

Org Lett. 2010 May 21;12(10):2294-7. doi: 10.1021/ol1006532.

Abstract

Ketones and acyl silanes were reduced to the corresponding alcohols by a simple procedure employing anti-1,3-diol and a catalytic amount (5 mol %) of 2,4-dinitrobenzenesulfonic acid in benzene at reflux. Asymmetric induction reached up to >99% ee when a chiral pentane-2,4-diol of 97% ee was used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Benzenesulfonates / chemistry*
  • Catalysis
  • Glycols / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Benzenesulfonates
  • Glycols
  • Ketones
  • Silanes
  • 2,4-dinitrobenzenesulfonic acid
  • 2,4-pentanediol