A General and Regioselective Synthesis of Cyclopentenone Derivatives through Nickel(0)-Mediated [3 + 2] Cyclization of Alkenyl Fischer Carbene Complexes and Internal Alkynes
| Autor: | Pablo Barrio, Luis A. López, Miguel Tomás, Lorena Riesgo, José Barluenga |
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| Rok vydání: | 2007 |
| Předmět: |
Cyclopentenone
chemistry.chemical_element Cyclopentanes Alkenes Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Chromium Colloid and Surface Chemistry Nickel Boron Transition metal carbene complex Regioselectivity Stereoisomerism General Chemistry Hydrocarbons Models Chemical chemistry Cyclization Alkynes Tin Methane Carbene Palladium |
| Zdroj: | Journal of the American Chemical Society. 129:14422-14426 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja075106+ |
| Popis: | A broad range of substituted 2-cyclopentenone derivatives 3-6 are synthesized by the nickel(0)-mediated [3 + 2] cyclization reaction of chromium alkenyl(methoxy)carbene complexes 1 and internal alkynes 2. The reaction takes place with complete regioselectivity with both unactivated alkynes and activated alkynes (electron-withdrawing and electron-donating substituted alkynes). Representative cycloadducts containing boron and tin substituents are further demonstrated to be active partners in classical Pd-catalyzed C-C coupling processes to allow the production of 2-aryl- and 2-alkynyl-substituted cyclopentenones 9-13. |
| Databáze: | OpenAIRE |
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