Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations
| Autor: | Chang Guo, Mirco Fleige, Constantin G. Daniliuc, Daniel Janssen-Müller, Frank Glorius |
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| Rok vydání: | 2016 |
| Předmět: |
Annulation
010405 organic chemistry Enantioselective synthesis General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences Benzazepine Umpolung chemistry.chemical_compound Colloid and Surface Chemistry chemistry Organocatalysis Organic chemistry Reactivity (chemistry) Carbene |
| Zdroj: | Journal of the American Chemical Society. 138:7840-7843 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | A combination of NHC organocatalysis and transition-metal catalysis gives rise to fundamentally new cooperative reactivity and enables the regio- and enantioselective annulation reaction between enals and vinyl benzoxazinanones. The cooperative umpolung annulation eliminates mutual deactivation and leads to a diverse set of benzazepine derivatives in good yields with excellent enantioselectivities (up to 99% ee). The development of such a cooperative catalytic system dramatically expands the scope of NHC organocatalysis by opening up new metal-catalyzed reaction pathways for homoenolate intermediates. |
| Databáze: | OpenAIRE |
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