Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.

Graphical abstractDiastereo- and enantioselective Henry reaction of nitroalkanes with aldehydes catalyzed by axially chiral guanidines is accomplished on the basis of complexation between chiral guanidinium and nitronate through two hydrogen bonds.Figure optionsDownload full-size imageDownload as PowerPoint slide