Advances in the construction of axially chiral biaryl-contained medium-sized rings <italic>via</italic> asymmetric catalysis

Medium-sized rings containing axially chiral biaryl units are a class of important chiral medium-sized cyclic compounds, which have attracted much attention owing to their unique structures and wide applications. In recent years, the rapid development of this area has been witnessed attributed to the great efforts from synthetic chemists through exploitation of new reagents, new reactions and effective synthesis strategies and catalyst systems. The transformations mainly include metal-catalyzed asymmetric hydrogenations and coupling reactions, organocatalytic asymmetric cyclizations and cascade reactions. In this review, the recent research progress on the catalytic asymmetric synthesis of axially chiral biaryl-contained medium-sized rings was highlighted according to the synthetic strategies: (1) aryl-aryl coupling, (2) side arm linking, (3) de novo construction of aryls, and (4) transformation of medium-sized rings. At the same time, the mechanism and stereoinduction of representative reactions are analyzed, and the present challenges and future development are discussed and prospected.