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Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones.

ABSTRACT: The enantioselective construction of densely functionalized cyclopentene bearing contiguous three stereocenters has been a challenging task in organic synthesis. Herein, we present a phoshine-catalyzed highly regio-, diastereo- and enantioselective [3 + 2] cycloaddition of γ-substituted allenoates with β-perfluoroalkyl enones, delivering a wide range of densely functionalized perfluoroalkylated cyclopentenes with three contiguous chiral stereocenters.

SUBMITTER: Zhou W

PROVIDER: S-EPMC5590097 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones.

Zhou Wei W Wang Huamin H Tao Mengna M Zhu Chao-Ze CZ Lin Tao-Yan TY Zhang Junliang J

Chemical science 20170419 6

The enantioselective construction of densely functionalized cyclopentene bearing contiguous three stereocenters has been a challenging task in organic synthesis. Herein, we present a phoshine-catalyzed highly regio-, diastereo- and enantioselective [3 + 2] cycloaddition of γ-substituted allenoates with β-perfluoroalkyl enones, delivering a wide range of densely functionalized perfluoroalkylated cyclopentenes with three contiguous chiral stereocenters. ...[more]

PMID: 28936335

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