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Modular, stereocontrolled Cβ-H/Cα-C activation of alkyl carboxylic acids.

Ming ShangKarla S FeuJulien C VantouroutLisa M BartonHeather L OsswaldNobutaka KatoKerstin GagaringCase W McNamaraGang ChenLiang HuShengyang NiPaula Fernández-CanelasMiao ChenRohan R MerchantTian QinStuart L SchreiberBruno MelilloJin-Quan YuPhil S Baran
Published in: Proceedings of the National Academy of Sciences of the United States of America (2019)
The union of two powerful transformations, directed C-H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus, amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series.
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