Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides

Org Biomol Chem. 2015 Feb 21;13(7):1969-73. doi: 10.1039/c4ob02398f.

Abstract

A synthesis of β-oxonitriles is reported via the generation of R(1)R(2)CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. (15)N- and (17)O-NMR data are reported for selected compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Cyanoketone / chemistry*
  • Methylation
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry

Substances

  • Amides
  • Nitriles
  • Cyanoketone