Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine

J Am Chem Soc. 2010 Feb 17;132(6):1802-3. doi: 10.1021/ja910831k.

Abstract

A convergent synthesis of (-)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

Publication types

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

MeSH terms

  • Alkynes / chemistry*
  • Amination
  • Carbodiimides / chemistry*
  • Guanidine / analogs & derivatives*
  • Guanidine / chemical synthesis
  • Guanidine / chemistry
  • Imidoesters / chemistry*
  • Pyrimidines / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Carbodiimides
  • Imidoesters
  • Pyrimidines
  • Spiro Compounds
  • crambidine
  • 2-aminopyrimidine
  • Guanidine