Catalytic C-H amination for the preparation of substituted 1,2-diamines

J Am Chem Soc. 2008 Aug 27;130(34):11248-9. doi: 10.1021/ja803344v. Epub 2008 Aug 5.

Abstract

Rhodium-catalyzed C-H insertion of hydroxylamine-derived sulfamate esters makes possible the synthesis of unique oxathiadiazinane heterocycles, which upon mild reduction furnish differentially substituted 1,2-diamine products. This highly chemo- and diastereoselective transformation underscores the power of catalytic C-H functionalization as a general approach to C-N bond construction.

Publication types

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

MeSH terms

  • Amination
  • Carbon / chemistry
  • Catalysis
  • Diamines / chemical synthesis*
  • Esters / chemistry*
  • Hydrogen / chemistry
  • Hydroxylamine / chemistry*
  • Models, Chemical
  • Nitrogen / chemistry
  • Oxidation-Reduction
  • Rhodium / chemistry*
  • Stereoisomerism
  • Sulfonamides / chemistry*

Substances

  • Diamines
  • Esters
  • Sulfonamides
  • Hydroxylamine
  • Carbon
  • Hydrogen
  • Rhodium
  • Nitrogen