A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones

J Am Chem Soc. 2015 Jun 24;137(24):7632-5. doi: 10.1021/jacs.5b04518. Epub 2015 Jun 12.

Abstract

The enantioselective addition of anilines to azoalkenes was accomplished through the use of a chiral phosphoric acid catalyst. The resulting α-arylamino hydrazones were obtained in good yields and excellent enantioselectivities and provide access to enantioenriched α-arylamino ketones. A serendipitous kinetic resolution of racemic α-arylamino hydrazones is also described.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry
  • Amination
  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / chemistry
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry
  • Hydrocarbons, Aromatic / chemical synthesis*
  • Hydrocarbons, Aromatic / chemistry
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Aniline Compounds
  • Hydrazones
  • Hydrocarbons, Aromatic
  • Ketones