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A Modular Approach to New Chiral Phosphorus Ligands for Enantioselective Catalytic Reactions


The discovery of truly efficient methods for gaining access to enantiomerically pure compounds in the development of pharmaceuticals, agrochemicals and flavours, has been a substantial challenge for chemists. Among the various ways to produce enantiopure compounds, enantioselective catalysis, using transition metal complexes of chiral ligands, constitutes a very appealing strategy as witnessed by the rapidly expanding number of publications in the field and the award of the Nobel Prize 2001 to W. S. Knowles, R. Noyori and K. B.Sharpless. The choice of an appropriate chiral ligand is perhaps most crucial, its structure being often the result of mechanistic knowledge, knowledge-based intuition or serendipity. In addition, an efficient enantioselective catalytic system is usually obtained after extensive trial-and-error optimisation of a number of concurrent factors (ligand structure, metal ion, stoichiometry, solvent, temperature, etc.). In such a complex scenario, the generation of chiral structures through a modular synthetic strategy (i.e. the coupling of different subunits) and high-throughput screening methodologies may be seen as a response to the requirement of new, more active and selective catalysts for organic transformations of interest. This project wishes to apply the techniques of \"combinatorial chemistry\" to the development of a new class of chiral phosphorus ligands. The aim of this project is therefore the design and synthesis of libraries of chiral 1,3-bis-sulfonyl-diazaphospholidines to be used as ligands for late transition metals in a number of interesting reactions (conjugate additions, allylic substitutions, hydrogenations, etc.). A modular approach to the synthesis of the ligands will be adopted, where the ligand structure will result from the assembling/coupling of the different components: a diamine scaffold, a sulfonyl chloride and the substitution at the phosphorus atom.

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