Highly enantioselective organocatalytic conjugate addition of nitromethane to benzylidene acetones.
Six active 4-aryl-5-nitro-pentan-2-ones were synthesized enantioselectively from the corresponding 5-aryl-butenones by asymmetric Michael addition of nitromethane using an imidazolidine-type enantioselective organocatalyst. The ee ratio of the products were between 67 and 100%, determined by HPLC with Chiracel OD. Molecular and crystal structure of 3,4-methylenedioxy-phenyl-5-nitro-pentan-2-one has been studied by single crystal X-ray diffraction.
Szántó
Gábor
G
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary. gszanto@mail.bme.hu
Bombicz
Petra
P
Grün
Alajos
A
Kádas
István
I
D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D002074:Butanones; D009574:Nitro Compounds; D009595:Nitroparaffins; C025383:benzylideneacetone; D008697:Methane; C008640:nitromethane