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.
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, Japan.
Hitoshi
H
Ube
Masahiro
M
Terada
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D006860:Hydrogen Bonding; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000447:Aldehydes; D009574:Nitro Compounds; D019791:Guanidine