The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of catalytic atroposelective approaches has been reported for the efficient construction of these challenging scaffolds. However, greatly concise and highly useful methodologies for the synthesis of these atropisomeric compounds, focusing on transition-metal, chiral amine, and phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly and systematically present all such reports by means of disclosing the mechanistic analysis and application, as well as the challenges and issues associated with the establishment of these atropisomers. In this review, we summarize the development of catalytic asymmetric synthetic strategies to access non-biaryl atropisomers rotating around a C–N chiral axis, including the reaction methods, mechanism, late-stage transformations, and applications.

Axial chirality exists ubiquitously in numerous natural products and has been extensively recognized for decades in pharmaceuticals and enantioselective transformations. The development of efficient methodologies to obtain enantiopure structures bearing...

Despite the remarkable advances in the research field of asymmetric catalytic oxidation reactions via hypervalent iodines with simple procedures, high level of efficiency and stereoselectivity over the past few decades, the development of their highly scalable, environmentally benign, and sustainable protocols under the greener organocatalysis paradigm for further industrial translations remains a long-standing synthetic organic chemistry and process engineering challenge. Herein, we design and synthesize a new library of conformationally flexible and recyclable aryl iodine catalysts by utilization of (i) industrial waste (chloramphenicol base) as the scaffold and (ii) inexpensive amino acid residue (threonine) as the chiral source. Our chiral aryl iodine(III) catalysts bearing H-bond donors and a tunable chiral pocket have been successfully applied in diverse robust asymmetric oxidative transformations, e.g., dearomatization, spirolactonization, direct C(sp2)−H/C(sp3)−H cross-coupling, and fluoridation. Our processes feature a column-isolation-free approach, easy-handling operation, and upscaling synthesis, with the catalysts being facilely recycled in particular via precipitation.