Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes

During efforts to expand the scope of Lewis-acid-catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol-% of MgI2 was used as a Lewis acid. It was also observed that the electronics of the nitrosoarene and judicious selection of the Lewis acid catalyst have a profound effect on the regioselectivity of the reaction

Strain-Promoted C-C Bond Cleavages of Cyclobutanes:A Molecular Complexity Generating Tool

The catalytic activation of carbon-carbon single bonds is a major challenge in organometallic chemistry, since the lack of prefunctionalization steps opens the way to new, economically and ecologically attractive reaction pathways. Strained ring substrates occupy a privileged role in C-C bond activations as the release of their ring strain facilitates the desired metal insertion. Important progress has been made in the field in the last decade. However, the development of asymmetric versions lags behind. This thesis shows the development of new methodologies for the enantioselective C-C bond activation of cyclobutane derivatives