Novel pyrrolidine-thiohydantoins/thioxotetrahydropyrimidinones as highly effective catalysts for the asymmetric Michael addition

Org Biomol Chem. 2011 May 7;9(9):3386-95. doi: 10.1039/c0ob01083a. Epub 2011 Mar 18.

Abstract

The synthesis of novel organocatalysts consisting of a pyrrolidine moiety and a thiohydantoin or a thioxotetrahydropyrimidinone ring is described. The compound combining the pyrrolidine with the thioxotetrahydropyrimidinone was found to be a highly effective catalyst for the Michael reaction. Low catalyst loadings (1-2.5%) can be employed leading to quantitative yields and excellent stereoselectivities in the reaction between cyclic ketones and nitroolefins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Pyrimidinones / chemistry*
  • Pyrrolidines / chemistry*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Thiohydantoins / chemistry*

Substances

  • Pyrimidinones
  • Pyrrolidines
  • Sulfhydryl Compounds
  • Thiohydantoins
  • tetrahydropyrimidinone
  • pyrrolidine