Development of tailor-made catalyst libraries for the construction of chiral C-X (X= C, N and O) bonds. Application to the synthesis of complex molecules

Identifier:  TDX:3287

Handle: https://hdl.handle.net/20.500.11797/TDX3287

Authors:  Joan, Saltó de la Torre

Abstract:
The constant demand for enantiomerically pure compounds (drugs, agrochemicals, additives ...) has driven the development of asymmetric catalysis using chiral organometallic compounds as catalysts. In this context, the synthesis of new chiral ligands is essential to discover good catalytic systems in asymmetric catalysis. This thesis has focused on the development of three new heterodonating chiral ligand libraries and their application to Pd-catalyzed allylic substitutions. These are ligand libraries stable in the air, easy to handle and have been synthesized in a few steps from readily available products and at low price. Combining theoretical studies and NMR spectroscopy, we were able to rationally fine-tune the ligands, improve enantioselectivity, and identify the species responsible for catalytic performance. In addition, the resulting allylic substitution products were successfully used for the synthesis of more complex molecules.