Asymmetric synthesis of α-alkyl α-selenocarbonyl compounds catalyzed by bifunctional organocatalysts

Org Lett. 2011 Jun 17;13(12):3052-5. doi: 10.1021/ol200923p. Epub 2011 May 17.

Abstract

A new organocatalytic approach for the synthesis of a variety of α-alkyl, α-phenylselenyl ketones as well as their corresponding esters and amides, by the addition of α-selenocarbonyl derivatives to nitroalkenes catalyzed by thiourea or squaramide cinchona catalysts, is presented. This catalytic system allows the preparation in high yields of enantiomerically enriched selenocarbonyl derivatives bearing two chiral centers with excellent ee's and dr's by using catalytic loadings of 3 mol%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Catalysis
  • Cinchona / chemistry
  • Combinatorial Chemistry Techniques
  • Esters
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Stereoisomerism
  • Thiourea / chemistry

Substances

  • Amides
  • Esters
  • Ketones
  • Organoselenium Compounds
  • Thiourea