Article

Annulation of Thiolmidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (-)-Crambidine

Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Journal of the American Chemical Society (Impact Factor: 11.44). 02/2010; 132(6):1802-3. DOI: 10.1021/ja910831k
Source: PubMed

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.

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