Litcius/Paper detail

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

2021Chemical Science90 citationsDOIOpen Access PDF

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