Novel chiral phosphine-phosphoramidite ligands derived from 1-naphthylamine for highly efficient Rh-catalyzed asymmetric hydrogenation

A new chiral phosphine-phosphoramidite ligand (S)-HY-Phos 1 has been prepared from 1-naphthylamine via a two-step transformation, and successfully applied in the Rh-catalyzed asymmetric hydrogenation of various functionalized olefins, including α-(acetamido)cinnamates, enamides and α-enol ester phosphonates, in which up to 98% ee, 99% ee and 99% ee were achieved, respectively.

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N-[1-(8-Diphenylphosphino)naphthyl]-(S)-1,10-bi-2-naphthylphosphoramiditeC42H29NO2P2[α]D20=+53.7 (c 0.56, CHCl3)Source of chirality: (S)-BINOLAbsolute configuration: (S)