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To explore the mechanism of silver and rhodium catalysis and reveal the origin of the chemo- and enantioselectivity of the reaction, density functional theory calculations were performed on the first silver-catalyzed highly enantioselective carbene transfer reaction. The calculation results reveal that when silver is used as a catalyst, due to the participation of the phosphate anion in the transition state, the enhanced nucleophilicity of the α-diazoacetamide unit promotes smooth dearomatization before generation of the silver carbene. Because the generated rhodium carbene has stronger electrophilicity, typical carbene reactions (C-H insertion and the Büchner reaction) are favored. In addition, in the process of silver catalyzed dearomatization, the formation of an R-type transition state is determined by the small torsion energy and strong interaction energy.

rsc advances

Theoretical study on the mechanism, chemo- and enantioselectivity of the Ag- <i>vs.</i> Rh-catalyzed intramolecular carbene transfer reaction of diazoacetamides

Theoretical study on the mechanism, chemo- and enantioselectivity of the Ag- vs. Rh-catalyzed intramolecular carbene transfer reaction of diazoacetamides