Fluorine effects in organocatalysis - asymmetric Brønsted acid assisted Lewis base catalysis for the synthesis of trifluoromethylated heterocycles exploiting the negative hyperconjugation of the CF3-group

Chem Commun (Camb). 2014 Jul 25;50(58):7889-92. doi: 10.1039/c4cc03229b.

Abstract

An efficient Brønsted acid assisted Lewis base catalysis protocol for the synthesis of enantiomerically pure trifluoromethylated dihydropyridazines starting from readily available hydrazones and α,β-unsaturated aldehydes has been developed. The reaction exhibits high tolerance towards many functional groups and is applicable to various aliphatic, aromatic and hetero-aromatic α,β-unsaturated aldehydes, and provides the products in good yields and with excellent enantioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Fluorine / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Hydrazones / chemistry*
  • Lewis Bases / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Heterocyclic Compounds
  • Hydrazones
  • Lewis Bases
  • Fluorine