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Ruthenium- and palladium-catalyzed enyne cycloisomerizations: differentially stereoselective syntheses of bicyclic structures.

ABSTRACT: Enyne cycloisomerizations can provide an efficient means for forming carbon-carbon bonds. We describe stereoselectively dichotomous enyne cycloisomerizations, entirely dependent on the selection of catalytic manifold. Ruthenium catalysis provides trans-fused bicyclic systems, whereas palladium catalysis provides the analogous cis-fused bicycles. A number of substrates are investigated, and the outcomes ultimately offer a clear mechanistic rationale for these observations.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2665024 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Ruthenium- and palladium-catalyzed enyne cycloisomerizations: differentially stereoselective syntheses of bicyclic structures.

Trost Barry M BM Ferreira Eric M EM Gutierrez Alicia C AC

Journal of the American Chemical Society 20081201 48

Enyne cycloisomerizations can provide an efficient means for forming carbon-carbon bonds. We describe stereoselectively dichotomous enyne cycloisomerizations, entirely dependent on the selection of catalytic manifold. Ruthenium catalysis provides trans-fused bicyclic systems, whereas palladium catalysis provides the analogous cis-fused bicycles. A number of substrates are investigated, and the outcomes ultimately offer a clear mechanistic rationale for these observations. ...[more]

PMID: 18998647

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