Modular, Stereocontrolled Cβ–H/Cα–C Activation of Alkyl Carboxylic Acids

Autor: Phil S. Baran, Jin-Quan Yu, Karla S. Feu, Lisa M. Barton, Bruno Melillo, Kerstin Gagaring, Rohan R. Merchant, Ming Shang, Miao Chen, Heather L. Osswald, Julien C. Vantourout, Gang Chen, Shengyang Ni, Stuart L. Schreiber, Paula Fernández-Canelas, Case W. McNamara, Tian Qin, Nobutaka Kato, Liang Hu
Rok vydání: 2019
Předmět:
Popis: 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.
Databáze: OpenAIRE