Palladium‐Catalyzed Atroposelective Kinetic C−H Olefination and Allylation for the Synthesis of C−B Axial Chirality
Jie Xu, Weihua Qiu, Xu Zhang, Zhihan Wu, Zhen Zhang, Kai Yang, Qiuling Song
Abstract
The direct C-H functionalization of 1,2-benzazaborines, especially asymmetric version, remains a great challenge. Here we report a palladium-catalyzed enantioselective C-H olefination and allylation reactions of 1,2-benzazaborines. This asymmetric approach is a kinetic resolution (KR), providing various C-B axially chiral 2-aryl-1,2-benzazaborines and 3-substituted 2-aryl-1,2-benzazaborines in generally high yields with excellent enantioselectivities (selectivity (S) factor up to 354). The synthetic potential of this reaction is showcased by late-stage modification of complex molecules, scale-up reaction, and applications.
Topics & Concepts
Kinetic resolutionEnantioselective synthesisPalladiumChemistryArylCatalysisChirality (physics)SelectivityAxial chiralitySurface modificationCombinatorial chemistryStereoisomerismStereochemistryOrganic chemistryPhysicsPhysical chemistryChiral symmetryAlkylNambu–Jona-Lasinio modelQuantum mechanicsQuarkAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacologyMolecular spectroscopy and chirality