Enantioselective palladaelectro-catalyzed C–H olefinations and allylations for N–C axial chirality
Uttam Dhawa, Tomasz Wdowik, Xiaoyan Hou, Binbin Yuan, João C. A. Oliveira, Lutz Ackermann
Abstract
Enantioselective palladaelectro-catalyzed C-H alkenylations and allylations were achieved with easily-accessible amino acids as transient directing groups. This strategy provided access to highly enantiomerically-enriched N-C axially chiral scaffolds under exceedingly mild conditions. The synthetic utility of our strategy was demonstrated by a variety of alkenes, while the versatility of our approach was reflected by atroposelective C-H allylations. Computational studies provided insights into a facile C-H activation by a seven-membered palladacycle.
Topics & Concepts
Enantioselective synthesisCatalysisChirality (physics)ChemistryAxial chiralityCombinatorial chemistryStereochemistryOrganic chemistryChiral symmetryPhysicsNambu–Jona-Lasinio modelQuantum mechanicsQuarkAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology