In a significant advancement for materials science, we have developed a new approach utilizing nitrogen-doped carbon dots (CDs) in enantioselective iminium-ion organocatalysis. The study explores the less-charted territory of enantioselective iminium ion nano-organocatalysis using CDs. Notably, nonchiral CDs with butylenediamine residues, combined with (S)-TRIP as a chiral phosphoric acid, demonstrated superior catalytic performance. A correlation between the features of the CDs’ surfaces and their catalytic performance was shown, and the catalytic activity of the employed CDs proved to be higher than that of simple molecular amines. An extensive reaction optimization allowed the reduction of different α,β-unsatured aldehydes in good yield and ee, using a low catalyst loading.
This research was developed in collaboration with Giacomo Filippini and Maurizio Prato, and egregiously led by Alessio Carioscia and Emanuele Cocco from our group. Maria Edith Casacchia, Giuliana Giorgianni, and Elena Incerto were also instrumental for the success of the project.
