A chiral rhodium carboxamidate catalyst for enantioselective C-H amination

J Am Chem Soc. 2008 Jul 23;130(29):9220-1. doi: 10.1021/ja8031955. Epub 2008 Jun 27.

Abstract

Rh2(S-nap)4, a chiral dirhodium tetracarboxamidate complex, has been developed and shown to be an effective catalyst for the asymmetric, intramolecular C-H amination of sulfamate esters. Enantiomeric excesses range from 60-99% for a collection of disparately substituted 3-arylpropylsulfamates. In addition, Rh2(S-nap)4 is found to promote chemoselective allylic C-H oxidation of unsaturated sulfamates, a property not observed with other dirhodium complexes tested to date.

Publication types

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

MeSH terms

  • Allyl Compounds / chemistry
  • Amides / chemistry
  • Amination
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Benzene Derivatives / chemistry
  • Carboxylic Acids / chemical synthesis
  • Catalysis
  • Esters / chemistry
  • Organometallic Compounds / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism
  • Sulfonic Acids / chemistry

Substances

  • Allyl Compounds
  • Amides
  • Amines
  • Benzene Derivatives
  • Carboxylic Acids
  • Esters
  • Organometallic Compounds
  • Sulfonic Acids
  • sulfamic acid
  • Rhodium