title: Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones.
abstract: The direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording alpha-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (-20 degrees C) was found to be a key for the successful alpha-aminoxylation of aldehydes, while slow addition of nitrosobenzene is essential for that of ketones. The scope of the reaction is presented.
authors.affiliation: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hayashi
authors.forename: Junichiro
authors.initials: J
authors.lastname: Yamaguchi
authors.forename: Tatsunobu
authors.initials: T
authors.lastname: Sumiya
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Hibino
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shoji
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000447:Aldehydes; D007659:Ketones; D009603:Nitroso Compounds; D011392:Proline; D010100:Oxygen; C012456:nitrosobenzene