Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides
Sen Zhang, Zhang‐Hong Luo, Wen-Tao Wang, Linghui Qian, Jia‐Yu Liao
Abstract
Herein, we report an unprecedented strategy for the simultaneous construction of a remote C–N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C–N atropisomers with the use of activated isocyanides.
Topics & Concepts
StereocenterChemistryAtropisomerCycloadditionArylEnantioselective synthesisCatalysisCombinatorial chemistryStereoselectivityChirality (physics)Substrate (aquarium)StereochemistryAxial chiralityOrganic chemistryOceanographyNambu–Jona-Lasinio modelAlkylPhysicsQuarkGeologyQuantum mechanicsChiral symmetry breakingAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityCatalytic C–H Functionalization Methods