Organocatalytic Enantioselective alpha-Nitrogenation of alpha,alpha- Disubstituted Aldehydes in the Absence of a Solvent
Torregrosa Chinillach, Alejandro
Carral Menoyo, Asier
Gomez Bengoa, Enrique
Chinchilla Cruz, Rafael
The Journal of Organic Chemistry 87(21) : 14507-14513 (2022)
A highly efficient enantioselective alpha-nitrogenation method of alpha,alpha-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresponding alpha,alpha- disubstituted alpha-nitrogenated aldehydes were obtained with excellent yields and enantioselectivities up to 99% ee. The sustainability of the procedure was established through the calculation of green metrics, such as EcoScale and E-factor. In addition, theoretical calculations have been used to justify the obtained enantioselectivity sense.