This doctoral thesis deals with the design of new catalytic systems for the synthesis of relevant chiral molecules from several approaches, including organocatalysis, continuous flow and nickel catalysis.
First, an immobilized organocatalyst was prepared for the enantioselective Robinson annulation reaction. With this new protocol, the desired chiral bicyclic enones are prepared in very short reaction times achieving excellent results. Moreover, a multigram-scale continuous-flow synthesis of these important products was successfully performed.
Secondly, a new class of organocatalysts was developed consisting of a C2-symmetric chiral triamine skeleton. This organocatalyst achieved improved diastereo- and enantioselectivities in comparison with its non-symmetric counterpart on the model aldol reaction of ketones and isatins.
Finally, a reductive [2+2] cycloaddition of alkynes towards the synthesis of cyclobutenes was discovered via nickel catalysis. The use of an unusual aminophosphine ligand was key to unravel this reactivity.