Stereoselective rhodium-catalyzed amination of alkenes

Org Lett. 2011 Oct 21;13(20):5460-3. doi: 10.1021/ol2021516. Epub 2011 Sep 15.

Abstract

The first stereoselective rhodium-catalyzed intermolecular aziridination and C-H amination of alkenes to produce chiral carbamate-protected aziridines and allylic amines is described. Good yields and diastereoselectivities were achieved using a readily available chiral N-tosyloxycarbamate and stoichiometric amount of the alkene substrate. Furthermore the protecting group is easy to cleave under mild reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amination
  • Aziridines / chemical synthesis
  • Aziridines / chemistry*
  • Carbamates / chemical synthesis
  • Carbamates / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Aziridines
  • Carbamates
  • Rhodium