BINOLrelated

BINOLrelated refers to compounds and families derived from BINOL, or 1,1'-bi-2-naphthol, or that share the BINOL framework. BINOL is an optically active, axially chiral diol consisting of two naphthol units linked at the 1 and 1' positions. The molecule exists as enantiomeric forms that can be resolved, and the two phenolic OH groups allow a wide range of derivatizations to produce chiral ligands, catalysts, or building blocks. As a result, BINOL-related compounds form a prominent class of chiral scaffolds in asymmetric synthesis.

BINOL derivatives are most widely known as ligands. A notable member is BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl), a chiral diphosphine used to induce enantioselectivity in metal-catalyzed reactions. Other BINOL-derived ligands include various phosphite and phosphoramidite derivatives, as well as substrates where the BINOL core is bonded to phosphine or other coordinating groups. The axial chirality of BINOL allows precise control of stereochemistry and provides a tunable pocket for substrate binding.

Applications span many areas of asymmetric catalysis, including hydrogenation, carbon–carbon bond forming reactions, and oxidative couplings. BINOL-related ligands enable high enantioselectivities and are used in both academic and industrial settings. The field continues to explore modifications at the 2,2' and 3,3' positions to adjust sterics and electronics, widening the scope of reactions that can be catalyzed with BINOL-derived systems.