(S)-BINAP
(S)-BINAP is the enantiopure (S)-enantiomer of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, a white to light yellow crystalline powder of 98% purity.
Its rigid binaphthyl framework fixes the two diphenylphosphine units in a defined helical arrangement, so metal complexes formed with it favour one face of a prochiral substrate and give the opposite configuration to the (R)-form. Because the two enantiomers are readily available, either antipode of a target molecule can be accessed from the same chemistry.
The compound is sensitive to air and moisture and should be kept under inert gas in a cool, dark place to preserve enantiomeric purity and colour.
• Asymmetric hydrogenation: ruthenium and rhodium complexes of (S)-BINAP hydrogenate β-keto esters, enamides and allylic alcohols with high enantioselectivity, giving the (S)-configured products.
• Enantiomer pairing: used as the mirror-image ligand to (R)-BINAP when the opposite absolute configuration is required in a synthetic route.
• Asymmetric addition and rearrangement: applied in enantioselective conjugate addition, hydroboration and sigmatropic rearrangement steps for chiral intermediates.
• Catalyst precursor chemistry: a standard ligand for preparing Noyori-type ruthenium catalysts and palladium complexes used in pilot-plant and commercial asymmetric processes.
Product Name: (S)-BINAP
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