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Cross-dehydrogenative coupling enables enantioselective access to CF₃-substituted all-carbon quaternary stereocenters.

ABSTRACT: A cross-dehydrogenative coupling strategy for enantioselective access to acyclic CF₃-substituted all-carbon quaternary stereocenters has been established. By using catalytic DDQ with MnO₂ as an inexpensive terminal oxidant, asymmetric cross coupling of racemic δ-CF₃-substituted phenols with indoles proceeded smoothly, providing CF₃-bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivities. The generality of the strategy is further demonstrated by efficient construction of all-carbon quaternary stereocenters bearing other polyfluoroalkyl and perfluoroalkyl groups such as CF₂Cl, C₂F₅, and C₃F₇.

SUBMITTER: Pan X

PROVIDER: S-EPMC8157275 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Pan Xiaoguang X Wang Zehua Z Kan Linglong L Mao Ying Y Zhu Yasheng Y Liu Lei L

Chemical science 20200129 9

A cross-dehydrogenative coupling strategy for enantioselective access to acyclic CF3-substituted all-carbon quaternary stereocenters has been established. By using catalytic DDQ with MnO2 as an inexpensive terminal oxidant, asymmetric cross coupling of racemic δ-CF3-substituted phenols with indoles proceeded smoothly, providing CF3-bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivities. The generality of the strategy ...[more]

PMID: 34084405

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