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Pentanidium-Catalyzed Direct Assembly of Vicinal All-Carbon Quaternary Stereocenters

Updated: Aug 12, 2022

Xu Ban, Yifan Fan, Tuan-Khoa Kha, Richmond Lee, Choon Wee Kee, Zhiyong Jiang and Choon-Hong Tan, CCS Chem. 2021, 3, 2192–2200


The stereoselective construction of vicinal all-carbon quaternary stereocenters has long been a formidable synthetic challenge. Direct asymmetric coupling of a tertiary carbon nucleophile with a tertiary carbon electrophile is the most straightforward approach, but it is sterically and energetically disfavoured. Herein, we describe a catalytic asymmetric substitution, where racemic tertiary bromides coupled directly with racemic secondary or tertiary carbanion, creating a series of congested C(sp3)-C(sp3) bonds, including isolated all-carbon quaternary stereocenters, vicinal tertiary/all-carbon quaternary stereocenters and vicinal all-carbon quaternary stereocenters. Using pentanidium as a catalyst, this double stereoconvergent process afforded substituted products in good enantioselectivities and diastereoselectivities.

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