Asymmetric enamide hydrogenation using phosphinite thioglycosides: synthesis of D- and L-aminoesters using D-sugars as catalyst precursors |
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| Authors: | Khiar Noureddine Navas Raquel Suárez Belén Alvarez Eleuterio Fernández Inmaculada |
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| Institution: | Instituto de Investigaciones Químicas, C.S.I.C-Universidad de Sevilla, c/. Américo Vespucio, 49, Isla de la Cartuja, 41092 Sevilla, Spain. khiar@iiq.csic.esinmaff@us.es |
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| Abstract: | Diastereomerically pure cationic Rh(I) complexes derived from phosphinite thioglycosides I were used as catalysts in highly enantioselective hydrogenations of enamides. The conformational similarity of alpha-D-arabinopyranose with beta-L-galactopyranose allows the synthesis of both enantiomers of alpha-amino acid derivatives such as D- and L-DOPA in excellent ee (97% and 98%), using derivatives of the former sugar as catalyst precursors. |
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