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

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.

SUBMITTER: Perl NR

PROVIDER: S-EPMC2839241 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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

Perl Nicholas R NR Ide Nathan D ND Prajapati Sudeep S Perfect Hahdi H HH Durón Sergio G SG Gin David Y DY

Journal of the American Chemical Society 20100201 6

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. ...[more]

PMID: 20095555

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