Abstract
The catalytic activity and stereoselectivity in the hydrogenation of itaconic and α-(acetylamino)cinnamic acids were studied in the presence of the complex [Rh(COD)(L1)2]+ TfO- (where COD is cyclooctadiene and L1 is (1S,2S,5R)-(+)-neomenthyldiphenylphosphine] which was generated in situ. The optical yield of the hydrogenation of itaconic acid increases both on addition of chiral (4S,5S)-(+)-2,2-dimethyl-4,5-bis(dimethylaminomethyl)-1,3-dioxolane (L2) as an auxiliary ligand to the complex [Rh(COD)(L1)2]+ TfO- and on addition of achiral and chiral tertiary phosphines to the complex [Rh(L2)2]+ TfO-. The result of joint action of two ligands can be regarded as "matched effect." Transformations of the complexes in a hydrogen atmosphere were examined by 1H and 3 1P NMR spectroscopy. It was found that at least three complexes: diamine complex [Rh(L2)2]+ TfO-, solvate complex [Rh(L1)2(solv)2]+ TfO-, and diamine-bis-phosphine complex [Rh(L1)2L2]+ TfO- may be catalytic precursors.
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Nindakova, L.O., Shainyan, B.A., Albanov, A.I. et al. Double Stereoselection in the Hydrogenation over Cationic Rh(I) Complexes with Two Different Chiral Ligands. Russian Journal of Organic Chemistry 39, 926–932 (2003). https://doi.org/10.1023/B:RUJO.0000003180.30666.61
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DOI: https://doi.org/10.1023/B:RUJO.0000003180.30666.61