Palladium-catalyzed olefin migration and 7- endo - trig cyclization of dehydroalanines
| Autor: | Ma. Carmen García-González, Eduardo Hernández-Vázquez, Luis D. Miranda, Fabio A. Vengochea-Gómez |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Olefin fiber Double bond 010405 organic chemistry Organic Chemistry chemistry.chemical_element 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Organopalladium Heck reaction Drug Discovery Ugi reaction Palladium |
| Zdroj: | Tetrahedron Letters. 59:848-852 |
| ISSN: | 0040-4039 |
| Popis: | 1,4- or 1,5-migration of a double bond of dehydroalanines under palladium catalysis is reported. The process occurred with several highly-substituted dehydroalanines under mild typical Heck reaction conditions. Although this was one of the first reports of a palladium-catalyzed 1,5-olefin migration, the outcome of the reaction was susceptible to the starting material. Mechanistically, the process involved a five- (1,4-migration) or six-membered ring (1,5-migration) organopalladium intermediate, which cleaved a C–N bond in an β-amino elimination process. |
| Databáze: | OpenAIRE |
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