Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides

Org Lett. 2011 Sep 16;13(18):4862-5. doi: 10.1021/ol201947b. Epub 2011 Aug 17.

Abstract

We describe here the first synthesis of N-phosphoryl ynamides featuring C- and P-chirality via copper(I)-catalyzed amidative cross-couplings between phosphoramidates and phosphordiamidates with alkynyl bromides. Also featured is a tandem aza-Claisen-hetero-[2+2] cycloaddition for the synthesis of N-phosphoryl azetidin-2-imines.

Publication types

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

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Catalysis
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Hydrocarbons, Brominated / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amides
  • Hydrocarbons, Brominated
  • Copper