Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions

Org Lett. 2008 Jun 19;10(12):2421-4. doi: 10.1021/ol8005826. Epub 2008 May 16.

Abstract

Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 degrees C to room temperature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Camphor / analogs & derivatives*
  • Camphor / chemistry*
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, Bridged-Ring / chemistry*
  • Hydrazines / chemical synthesis
  • Hydrazines / chemistry*
  • Molecular Structure
  • Salts
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, Bridged-Ring
  • Hydrazines
  • Salts
  • brine
  • hydrazine
  • Camphor