Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines

J Am Chem Soc. 2012 Mar 28;134(12):5440-3. doi: 10.1021/ja211880s. Epub 2012 Mar 20.

Abstract

Asymmetric epoxidation of allylic and homoallylic amine derivatives catalyzed by Hf(IV)-bishydroxamic acid complexes is described. Under similar conditions, aldimine and ketimine produced oxaziridines. The sulfonyl group is demonstrated to be an effective directing group for these transformations.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Aziridines / chemical synthesis
  • Catalysis
  • Epoxy Compounds / chemistry*
  • Hafnium / chemistry*
  • Hydroxamic Acids / chemistry*
  • Imines / chemistry*
  • Stereoisomerism
  • Sulfonamides / chemistry*

Substances

  • Amines
  • Aziridines
  • Epoxy Compounds
  • Hydroxamic Acids
  • Imines
  • Sulfonamides
  • Hafnium