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

Nicholas R Perl, Nathan D Ide, Sudeep Prajapati, Hahdi H Perfect, Sergio G Durón, David Y Gin

Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.

Journal of the American Chemical Society 2010 Feb 17

filter terms:

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.

Citation

Nicholas R Perl, Nathan D Ide, Sudeep Prajapati, Hahdi H Perfect, Sergio G Durón, David Y Gin. Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine. Journal of the American Chemical Society. 2010 Feb 17;132(6):1802-3