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UBC Theses and Dissertations

Synthesis of chiral ferrocenylphosphine complexes of rhodium (I) and their use as catalysts for homogeneous asymmetric hydrogenation Yeh, Eshan


The present work was directed toward the synthesis of a new chiral catalyst for asymmetric homogeneous hydrogenation. Efficient ways to synthesize the ferrocenylphosphine ligands (R,S)- and (S,R)-⍺-[2-diphenylphosphinoferrocenyl]ethyldimethylamine ((R,S)- and (S,R)-FcNP) and their cationic rhodium complexes [(diene)Rh(±)FcNP]⁺A⁻ were developed. Structural data for the ligand and models of its metal complex have been used to rationalize the stereochemical approach of the substrate to the metal complex, and hence predict the absolute configuration of the product. The rate of catalytic hydrogenation is dependent on the substrate as is the optical yield of the product alkane. High optical yields are obtained when ⍺-acetamidocinnamlc acid is hydrogenated at 1 atm H₂ and 32°.

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