π-Coordinating Chiral Primary Amine/Palladium Synergistic Catalysis for Asymmetric Allylic Alkylation
| Autor: | Sanzhong Luo, Yaning Wang, Junli Chai, Jie Zhang, Long Zhang, Xueling Mi, Chang You |
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| Rok vydání: | 2020 |
| Předmět: |
inorganic chemicals
Primary (chemistry) Ligand Chemistry organic chemicals chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis 0104 chemical sciences Tsuji–Trost reaction Colloid and Surface Chemistry Synergistic catalysis Amine gas treating Palladium |
| Zdroj: | Journal of the American Chemical Society. 142:3184-3195 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | We report an arene-containing chiral primary amine as a dual aminocatalyst and ligand: the π-coordinating aminocatalyst/palladium synergistic catalysis for asymmetric allylic alkylation of α-branched β-ketocarbonyls. The use of arene-containing chiral primary amine catalyst led to not only enhanced reaction rate but also reversed chiral induction compared with its sterically bulky derivative. Both enantiomers of the allylic adducts bearing acyclic all-carbon quaternary stereocenters could be obtained from the same configured chiral aminocatalysts with high efficiency and excellent regio-, stereo-, and enantioselectivity. Mechanistic studies revealed a distinctive Pd-arene π-coordination mode for effective catalysis. The π-coordinating chiral primary amine catalyst could be successfully applied in the asymmetric allylation reactions of vinylethylene carbonates, vinyl epoxides, or simple allylic alcohols. |
| Databáze: | OpenAIRE |
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