C2-symmetric diphosphinite ligands derived from carbohydrates. The strong influence of remote stereocenters on asymmetric rhodium-catalyzed hydrogenation |
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Authors: | Aghmiz Mohamed Aghmiz Ali Díaz Yolanda Masdeu-Bultó Anna Claver Carmen Castillón Sergio |
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Institution: | Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, Pl. Imperial Tarraco 1, 43005 Tarragona, Spain. |
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Abstract: | Modular ligands of C(2) symmetry (13a-e, 14a,b,d, and ent-9), systematically modified at positions 2 and 5, were easily prepared from d-glucosamine, D-glucitol, and tartaric acid, respectively. The application of these ligands in the rhodium-catalyzed hydrogenation of methyl acetamidoacrylate, methyl acetamidocinnamate, and dimethyl itaconate shows that both the configuration and the substituents at positions 2 and 5 of the tetrahydrofuran backbone have a strong influence on the enantioselectivty of the processes. |
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