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Gold‐Catalyzed [4C+3C] Intramolecular Cycloaddition of Allenedienes: Synthetic Potential and Mechanistic Implications |
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| Authors: | Beatriz Trillo Fernando López Dr. Sergi Montserrat Gregori Ujaque Dr. Luis Castedo Prof. Dr. Agustí Lledós Prof. Dr. Jose L. Mascareñas Prof. Dr. |
| Affiliation: | 1. Departamento de Química Orgánica, Universidad de Santiago de Compostela, Facultad de Química, 15782, Santiago de Compostela (Spain), Fax: (+34)?981‐595012;2. Instituto de Química Orgánica General (CSIC), Juan de la Cierva, 3, 28006, Madrid (Spain);3. Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona (Spain) |
| Abstract: | Efficient at room temperature : The Au complex generated in situ from [(IPr)AuCl] and AgSbF6 promotes the [4C+3C] intramolecular cycloaddition of allenes and dienes at room temperature, and in a particularly efficient and versatile manner. A DFT study on dimethylallenyl precursors agreed with the formation and cycloaddition of a metal–allyl cation intermediate, and points to the 1,2‐hydride shift as the key rate‐limiting step.  |
| Keywords: | allenes carbocycles cycloaddition density functional calculations gold homogeneous catalysis |