Cobalt-catalyzed asymmetric olefin aziridination with diphenylphosphoryl azide

J Org Chem. 2008 Sep 19;73(18):7260-5. doi: 10.1021/jo801151x. Epub 2008 Aug 19.

Abstract

The cobalt(II) complexes of D2-symmetric chiral porphyrins, such as 3,5-Di(t)Bu-ChenPhyrin P5, can catalyze asymmetric olefin aziridination with diphenylphosphoryl azide (DPPA) as a nitrene source. Acceptable asymmetric inductions were observed for the [Co(P5)]-based catalytic system, forming the desired N-phosphorus-substituted aziridines in moderate to high yields and good enantioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Azides / chemistry*
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Catalysis
  • Cobalt / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Porphyrins / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Azides
  • Aziridines
  • Organometallic Compounds
  • Porphyrins
  • Cobalt
  • diphenylphosphorazidate