Enantioselective Formation of All-Carbon Quaternary Stereocenters in gem-Difluorinated Cyclopropanes via Rhodium-Catalyzed Stereoablative Kinetic Resolution

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Enantioselective Formation of All-Carbon Quaternary Stereocenters in gem-Difluorinated Cyclopropanes via Rhodium-Catalyzed Stereoablative Kinetic Resolution

Jiang, Zhong-Tao; Chen, Zhengzhao; Zeng, Yaxin; Shi, Jiang-Ling; Xia, Ying

Organic letters, 08/2022, Volume: 24, Issue: 33

Journal Article

Herein, we report an effective method to offer chiral gem-difluorinated cyclopropanes containing an all-carbon quaternary stereocenter by rhodium-catalyzed stereoablative kinetic resolution. The activation of a sterically hindered all-carbon quaternary C–C bond through oxidative addition with a chiral rhodium complex is proposed as the enantiodetermining step. A wide range of gem-difluorinated cyclopropanes can be obtained with excellent ee values (ee = 87% to >99.9%), which are demonstrated to be useful chiral fluorine-containing building blocks by a series of postfunctionalizations.

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Jiang, Zhong-Tao | Chen, Zhengzhao | Zeng, Yaxin | Shi, Jiang-Ling | Xia, Ying

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