Get access

Carbohydrates as Building Blocks of Privileged Ligands for Multiphasic Asymmetric Catalysis

Authors

  • Vincenzo Benessere,

    1. Dipartimento di Chimica “Paolo Corradini”, Università di Napoli “Federico II”, Complesso Universitario di Monte S. Angelo via Cintia, 80126 Napoli, Italy, Fax: (+39) 081674090
    Search for more papers by this author
  • Antonella De Roma,

    1. Dipartimento di Chimica “Paolo Corradini”, Università di Napoli “Federico II”, Complesso Universitario di Monte S. Angelo via Cintia, 80126 Napoli, Italy, Fax: (+39) 081674090
    Search for more papers by this author
  • Francesco Ruffo Prof. Dr.

    1. Dipartimento di Chimica “Paolo Corradini”, Università di Napoli “Federico II”, Complesso Universitario di Monte S. Angelo via Cintia, 80126 Napoli, Italy, Fax: (+39) 081674090
    Search for more papers by this author

Abstract

To combine the high chemical performance of asymmetric catalysis with the increasing need for sustainability, a strategy is presented that involves the straightforward preparation of “Trost”-like ligands suitable for application in multiphasic homogeneous catalysis. Ligands with coordinating functions (phosphinoamide-phoshinoester groups) as well as phase tags introduced on a D-glucose scaffold were prepared and then examined in the Pd-catalysed asymmetric desymmetrization of meso-2-cyclopenten-1,4-diol biscarbamate. In line with our assumption, the performance of the catalyst system under traditional conditions is as high as that of the original Trost ligand, derived from trans-cyclohexanediamine, giving enantioselectivities of 98 % ee. Moreover, promising results were observed under multiphasic homogeneous conditions.

Ancillary