Asymmetric Palladium-Catalyzed Allylic Alkylation Using Dialkylzinc Reagents: A Remarkable Ligand Effect
| Autor: | Marco Luparia, Supaporn Niyomchon, Nuno Maulide, Antonio Misale |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
inorganic chemicals
Allylic rearrangement 010405 organic chemistry Stereochemistry organic chemicals Enantioselective synthesis food and beverages chemistry.chemical_element General Chemistry Alkylation Diethylzinc 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Umpolung Tsuji–Trost reaction chemistry.chemical_compound chemistry Electrophile Palladium |
| Zdroj: | Angewandte Chemie International Edition. 53:7068-7073 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201309074 |
| Popis: | A serendipitously discovered palladium-catalyzed asymmetric allylic alkylation reaction with diorganozinc reagents, which displays broad functional group compatibility, is reported. This novel transformation hinges on a remarkable ligand effect which overrides the standard "umpolung" reactivity of allyl-palladium intermediates in the presence of dialkylzincs. Owing to its mild conditions, enantioselective allylic alkylations of racemic allylic electrophiles are possible in the presence of sensitive functional groups. |
| Databáze: | OpenAIRE |
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