Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation

J Am Chem Soc. 2008 Jul 9;130(27):8590-1. doi: 10.1021/ja8027394. Epub 2008 Jun 13.

Abstract

This paper describes a catalytic asymmetric diamination process for terminal olefins at allylic and homoallylic carbons via formal C-H activation using di-tert-butyldiaziridinone as nitrogen source with a catalyst generated from Pd2(dba)3 and chiral phosphorus amidite ligand. A wide variety of readily available terminal olefins can be effectively diaminated in good yields with high regio-, diastereo-, and enantioselectivities.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Aziridines / chemistry
  • Carbon / chemistry
  • Catalysis
  • Diamines / chemical synthesis*
  • Diamines / chemistry
  • Hydrogen / chemistry
  • Ligands
  • Molecular Structure
  • Naphthalenes / chemistry
  • Nitrogen / chemistry
  • Organometallic Compounds / chemistry*
  • Phosphorus / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Aziridines
  • Diamines
  • Ligands
  • Naphthalenes
  • Organometallic Compounds
  • S(-)2,2'-dihydroxy-1,1'-binaphthyl
  • di-tert-butyldiaziridinone
  • Phosphorus
  • Carbon
  • Hydrogen
  • Nitrogen