Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.
The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with alpha-ketoesters catalyzed by a new C6'-OH cinchona alkaloid catalyst. This is the first highly efficient organocatalytic asymmetric Henry reaction with ketones. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of alpha-ketoesters.
Li
Hongming
H
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Wang
Baomin
B
Deng
Li
L
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D002930:Cinchona Alkaloids; D004952:Esters; D007659:Ketones; D009574:Nitro Compounds