Carbohydrates as building blocks of privileged ligands for multiphasic asymmetric catalysis

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.