Direct Access of the Chiral Quinolinyl Core of Cinchona Alkaloids via a Brønsted Acid and Chiral Amine Co-catalyzed Chemo- and Enantioselective α-Alkylation of Quinolinylmethanols with Enals
| Autor: | Mengchao Tong, Cong Qin, Wei Wang, Sinan Wang, Jinchen Zhuang, Hao Li |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Quinoline Enantioselective synthesis Iminium Total synthesis Cinchona Alkaloids Alkylation 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Brønsted–Lowry acid–base theory |
| Zdroj: | Organic Letters. 20:1195-1199 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A strategy for the facile construction of the chiral quinolinylmethanolic structure, a core featured in cinchona alkaloids, is reported. A new reactivity is harnessed by TfOH-promoted chemoselective activation of α-C-H over O-H bond in quinolinylmethanols. The new reactivity is successfully engineered with an iminium catalysis in a synergistic manner to create a powerful conjugate addition-cyclization cascade process for synthesis of chiral quinoline derived γ-butyrolactones in good yields and with good to excellent enantioselectivities. The method enables the first total synthesis of natural product broussonetine in three steps. |
| Databáze: | OpenAIRE |
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