Rhodium(III)-Catalyzed Atroposelective Synthesis of C–N Axially Chiral Naphthylamines and Variants via C–H Activation
Peiyuan Wang, Yaling Huang, Jierui Jing, Fen Wang, Xingwei Li
Abstract
Reported herein is the efficient and atroposelective construction of two categories of C-N atropisomers via rhodium(III)-catalyzed C-H activation of sulfoxonium ylides en route to [4+2] annulation with sterically hindered, electron-rich alkynes. This reaction proceeds with high regio- and enantioselectivity under redox-neutral conditions via a double-substrate activation strategy, providing a novel entry to C-N axially chiral 4-functionalized 1-naphthols.
Topics & Concepts
AtropisomerChemistryAnnulationRhodiumCatalysisSteric effectsSubstrate (aquarium)StereochemistryCombinatorial chemistryYield (engineering)Medicinal chemistryOrganic chemistryMaterials scienceGeologyMetallurgyOceanographyAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology