Direct Proline-Catalyzed Asymmetric α-Aminoxylation of Aldehydes and Ketones

Direct Proline-Catalyzed Asymmetric α-Aminoxylation of Aldehydes and Ketones

The direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording α-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (−20 °C) was foun...

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Veröffentlicht in:Journal of organic chemistry 2004-09, Vol.69 (18), p.5966-5973
Hauptverfasser: Hayashi, Yujiro, Yamaguchi, Junichiro, Sumiya, Tatsunobu, Hibino, Kazuhiro, Shoji, Mitsuru
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Aliphatic compounds
Catalysis
Chemistry
Exact sciences and technology
Ketones - chemistry
Models, Molecular
Molecular Structure
Nitroso Compounds - chemistry
Organic chemistry
Oxygen - chemistry
Preparations and properties
Proline - chemistry
Stereoisomerism
Temperature
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Beschreibung
Zusammenfassung:The direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording α-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (−20 °C) was found to be a key for the successful α-aminoxylation of aldehydes, while slow addition of nitrosobenzene is essential for that of ketones. The scope of the reaction is presented.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049338s