Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones

Using newly designed alpha-imino amide surrogates and azlactones as amphiphilic reactants, catalyzed by a chiral bifunctional guanidine, the construction of chiral 3,4-diaminopyrrolidine-2,5-diones and their derivatives was realized via formal [3+2]-cyclization. The role of guanidine as a multiple hydrogen bond donor was demonstrated by DFT calculations.

Automated summary

By utilizing newly designed alpha-imino amide surrogates and azlactones as reactants, catalyzed by a chiral bifunctional guanidine, the construction of chiral 3,4-diaminopyrrolidine-2,5-diones and their derivatives was achieved through formal [3+2]-cyclization. The DFT calculations confirmed the role of guanidine as a multiple hydrogen bond donor.