Sugar-based ligand libraries for asymmetric reductions and c-c bond forming reactions

Identifier:  TDX:1025

Handle: https://hdl.handle.net/20.500.11797/TDX1025

Authors:  Coll Serrahima, Mª Mercè

Abstract:
One of the main methods for producing enantiomerically pure compounds is metal asymmetric catalysis. An important step in this strategy is the design and preparation of chiral ligands. In this context, we have developed new chiral ligands for several important asymmetric catalytic reactions. Specifically we have focused on: (a) The application of a furanoside phosphite-phosphoroamidite and diphosphoroamidite ligand library in the hydrogenation of prochiral olefins. These ligands have provided excellent enantioselectivities (up to >99% ee). (b) The application of furanoside thioether-phosphite, thioether-phosphinite and thioether-phosphoroamidite ligand libraries in the challenging Ir-catalyzed hydrogenation of unfunctionalized olefins and in Pd-allylic substitution reactions. The results in hydrogenation compete favourable with the best ones previously reported. (c) The application of carbohydrate-based pseudo-dipeptide and thioamide ligand libraries in transfer hydrogenation of ketones. The results again compete favourable with the best one previously reported. Unprecedent enzyme-like behaviour has been obtained, providing ee’s up to 99% for a wide range of substrates.