title: Catalytic enantioselective difluoroalkylation of aldehydes.
abstract: Copper-catalyzed bond scission of pentafluorobutane-1,3-diones generates difluoroenolates that react with aldehydes to give a wide range of chiral α,α-difluoro-β-hydroxy ketones within a few hours in up to 99 % yield and 92 % ee. The synthetic utility of this reaction is demonstrated with the stereoselective synthesis of a chiral anti-1,3-diol exhibiting a central difluoromethylene unit and efficient conversion to a 2,2-difluoro-3-hydroxy carboxylic acid.
authors.affiliation: Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057, USA.
authors.forename: Peng
authors.initials: P
authors.lastname: Zhang
authors.forename: Christian
authors.initials: C
authors.lastname: Wolf
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D006845:Hydrocarbons, Fluorinated; D003300:Copper
keywords: aldol reaction; asymmetric catalysis; cleavage reactions; fluoroenolates; reactive intermediates