Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes
Uttam Dhawa, Cong Tian, Tomasz Wdowik, João C. A. Oliveira, Jiping Hao, Lutz Ackermann
Abstract
Asymmetric pallada-electrocatalyzed C-H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective C-H activations were realized with high position-, diastereo-, and enantio-control under mild reaction conditions to obtain highly enantiomerically-enriched biaryls and fluorinated N-C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel chiral BINOLs, dicarboxylic acids and helicenes of value to asymmetric catalysis. Mechanistic studies by experiments and computation provided key insights into the catalyst's mode of action.
Topics & Concepts
Enantioselective synthesisCatalysisTransient (computer programming)Combinatorial chemistryChemistryStereochemistryComputer scienceOrganic chemistryOperating systemAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsMolecular spectroscopy and chirality