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

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

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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Veröffentlicht in:Journal of the American Chemical Society 2010-02, Vol.132 (6), p.1802-1803
Hauptverfasser: Perl, Nicholas R, Ide, Nathan D, Prajapati, Sudeep, Perfect, Hahdi H, Durón, Sergio G, Gin, David Y
Format: Artikel
Sprache:eng
Schlagworte:
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
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Beschreibung
Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja910831k