title: A new class of urea-substituted cinchona alkaloids promote highly enantioselective nitroaldol reactions of trifluoromethylketones.
abstract: The first class of bifunctional cinchona-alkaloid catalysts incorporating a urea moiety at C-5' has been developed. These materials catalyze the efficient and highly enantioselective 1,2-addition of nitromethane to trifluoromethylketones to form synthetically pliable products incorporating a quaternary stereocenter. Excellent product yields and levels of enantiomeric excess are possible, and the optimum catalyst structure is capable of promoting the Henry reaction involving alkyl trifluoromethylketones with unprecedented enantioselectivity.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
authors.forename: Carole
authors.initials: C
authors.lastname: Palacio
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Connon
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry* / Q000145:classification; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D002930:Cinchona Alkaloids; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D009574:Nitro Compounds; D014508:Urea