The Use of Chiral ortho‐Auxiliaries/Substituents and Remote Stereogenic Centers in Atropselective Biaryl Synthesis

• Published in: European journal of organic chemistry Vol. 2020; no. 2; pp. 147 - 155
• Main Author: Nguyen, Thien T.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 16.01.2020
• Subjects: Atropselectivity; Biaryl synthesis; Chirality; Chirality transfer; Ligands; Natural products; Organic chemistry; ortho‐Auxiliary; Phosphines; Remote asymmetric induction
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201901557

Axially chiral biaryls are core structures of increasingly important organic molecules including bioactive natural products, drugs, chiral ligands and organocatalysts. Among established methods for accessing these axially chiral structures, chiral ortho‐auxiliaries/substituents and remote stereogenic centers have provided useful strategies for the preparation of highly functionalized enantiopure biaryl compounds such as gossypol, rugulotrosin A, korupensamine A, phosphine ligands, sulfoxides, and 2‐amino‐2′‐hydroxy‐1,1′‐binaphthyls (NOBINs). These strategies, which entail point‐to‐axial chirality transfer, have received increasing attention in the last thirty years. This minireview up to October 2019 describes these methods with attention to the atropselective formation of biaryl systems influenced by chiral ortho‐auxiliaries/substituents and remote stereogenic centers. Two strategies for establishing a chiral axis for biaryl synthesis with significant levels of atropselectivity via a wide range of organic reactions have been developed. These methods have provided access to important ligands, catalysts, natural products, and bioactive drugs. This minireview describes these methods and their potentials for atropselective synthesis.