Oxidative enantioselective α-fluorination of aliphatic aldehydes enabled by N-heterocyclic carbene catalysis

Angew Chem Int Ed Engl. 2015 Jan 7;54(2):656-9. doi: 10.1002/anie.201409473. Epub 2014 Oct 27.

Abstract

Described is the first study on oxidative enantioselective α-fluorination of simple aliphatic aldehydes enabled by N-heterocyclic carbene catalysis. N-fluorobis(phenyl)sulfonimide serves as a an oxidant and as an "F" source. The C-F bond formation occurs directly at the α position of simple aliphatic aldehydes, thus overcoming nontrivial challenges, such as competitive difluorination and nonfluorination, and proceeds with high to excellent enantioselectivities.

Keywords: N-heterocyclic carbenes; aldehydes; enolates; fluorine; oxidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Fluorine / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Aldehydes
  • Heterocyclic Compounds
  • carbene
  • Fluorine
  • Methane