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  • Title: C2-symmetric diphosphinite ligands derived from carbohydrates. The strong influence of remote stereocenters on asymmetric rhodium-catalyzed hydrogenation.
    Author: Aghmiz M, Aghmiz A, Díaz Y, Masdeu-Bultó A, Claver C, Castillón S.
    Journal: J Org Chem; 2004 Oct 29; 69(22):7502-10. PubMed ID: 15497975.
    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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