Kinetic Resolution of Unprotected BINOLs via Lewis Base-Catalyzed O-Boc Protection

A Lewis base-catalyzed kinetic resolution of 1,1’-bi-2,2’-naphthols (BINOLs) through atroposelective O-Boc protection is described. Using a commercially available biscinchona alkaloid catalyst, a broad range of unprotected BINOLs undergo selective transformation with Boc anhydride (Boc 2 O) to deliver enantioenriched BINOLs with selectivity factors ( s ) up to 78. The resulting enantioenriched BINOLs can be further diversified by transition-metal-catalyzed cross-coupling reactions, providing streamlined access to structurally varied BINOL analogs.