Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones.
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.
Hayashi
Yujiro
Y
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
Yamaguchi
Junichiro
J
Sumiya
Tatsunobu
T
Hibino
Kazuhiro
K
Shoji
Mitsuru
M
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
D000447:Aldehydes; D007659:Ketones; D009603:Nitroso Compounds; D011392:Proline; D010100:Oxygen; C012456:nitrosobenzene