Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines

Chiral phosphoric acid based organocatalysis and visible-light photocatalysis have both emerged as promising technologies for the sustainable production of fine chemicals. In this context, we have envisioned the design and the synthesis of a new class of chimeric catalytic entities that would feature both catalytic capabilities. Given their multitask nature, such catalysts would be particularly attractive for the development of new catalytic transformations, tandem processes in particular. Toward this goal, several BINOL-based chiral phosphoric acid backbones presenting one or two visible-light-sensitive thioxanthone moieties have been prepared and studied. The utility of these new photoactive chiral organocatalysts is then demonstrated in the enantioselective tandem three-component electrophilic amination of enecarbamates. Of note, the C 1 -symmetric organo/photocatalyst has shown a better catalytic activity than those presenting a C 2 symmetry.