This C2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism).

The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings.

[1] BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium.

[3][4] Silver complexes are also important; BINAP-AgF can be used to enantioselectively protonate silyl enol ethers.

[5] Subsequent studies revealed that related diphosphines with a narrower dihedral angle between the aromatic faces give catalysts that are more enantioselective.