Axially Chiral Copper Catalyst for Asymmetric Synthesis of Valuable Diversely Substituted BINOLs

Abstract

Optically pure BINOL (1,1′-bi-2-naphthol) and diversely substituted BINOLs are highly valuable chiral motifs featuring axial chirality widely applied in various fields. Although unsubstituted BINOL is commercially available, the catalytic asymmetric synthesis of optically pure diversely substituted BINOLs is still very challenging. Herein, we report the development of a highly enantioselective dinuclear copper catalyst for oxidative homo- and cross-coupling of a variety of 2-naphthols to provide access to a broad range of highly valuable diversely substituted C 2 - and C 1 -symmetric BINOLs in up to 92% yield with high enantioselectivities (up to 99.5:0.5 er).

Topics & Concepts