Copper(I) catalyzed regioselective asymmetric alkoxyamination of aryl enamide derivatives

Org Lett. 2011 Nov 4;13(21):5792-5. doi: 10.1021/ol202367d. Epub 2011 Oct 5.

Abstract

The copper(I) catalyzed reaction of an enamide with an iminoiodane, in the presence of an alcohol, triggers the direct alkoxyamination of the double bond. This transformation represents a straightforward access to α-amino aminals in a completely regio- and diastereoselective manner. Use of a chiral Box ligand allows this reaction to be carried out in an enantioselective fashion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Amides / chemistry*
  • Amination
  • Catalysis
  • Copper / chemistry*
  • Ligands
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alcohols
  • Amides
  • Ligands
  • alkoxyl radical
  • Copper