Gold‐ or Platinum‐Catalyzed Cascade Processes of Alkynol Derivatives Involving Hydroalkoxylation Reactions Followed by Prins‐Type Cyclizations |
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Authors: | José Barluenga Prof. Dr. Amadeo Fernández Alejandro Diéguez Dr. Félix Rodríguez Dr. Francisco J. Fañanás Dr. |
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Affiliation: | Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34)?985103450 |
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Abstract: | An efficient method for the synthesis of [3.3.1]bicyclic compounds from easily available alkynol derivatives has been developed. The reaction is based on a gold‐ or platinum‐catalyzed tandem process that involves an intramolecular hydroalkoxylation of a triple bond followed by a Prins‐type cyclization. The reaction has been carried out with differently substituted alkynol derivatives and oxygen‐, nitrogen‐, and carbon‐centered nucleophiles. The incorporation of halogen atoms as nucleophiles and elimination reactions has also been studied. Enantiomerically pure [3.3.1]bicyclic systems were easily synthesized from the chiral pool. |
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Keywords: | bicyclic systems cascade reactions catalytic synthesis cyclization gold platinum |
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