title: Catalytic enantioselective O-nitrosocarbonyl aldol reaction of β-dicarbonyl compounds.
abstract: The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched α-hydroxy-β-ketoesters including the antibacterial natural product kjellmanianone (up to 99% ee). MnO(2) was introduced as a mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.
authors.affiliation: Department of Chemistry, The University of Chicago, Illinois 60637, United States.
authors.forename: Mahiuddin
authors.initials: M
authors.lastname: Baidya
authors.forename: Kimberly A
authors.initials: KA
authors.lastname: Griffin
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D004952:Esters; D007659:Ketones; D009603:Nitroso Compounds; D009942:Organometallic Compounds; D003300:Copper