Prolinethiol ether catalysis in an asymmetric Michael reaction: solvent-free synthesis of functionalized monohaloalkenes

J Org Chem. 2013 Feb 1;78(3):1254-9. doi: 10.1021/jo302288z. Epub 2013 Jan 10.

Abstract

The organocatalytic Michael reaction of ketones with γ-monohalonitrodienes catalyzed by chiral prolinethiol ether under solvent-free conditions was developed. The described method represents a novel approach for accessing highly functionalized monohaloalkenes with α, β-stereocenters of up to >99% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry*
  • Catalysis
  • Ether / chemistry*
  • Hydrocarbons, Halogenated / chemical synthesis*
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Proline / chemistry*
  • Solvents / chemistry*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*

Substances

  • Alkenes
  • Hydrocarbons, Halogenated
  • Solvents
  • Sulfhydryl Compounds
  • Ether
  • Proline