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Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones.
J Org Chem. 2004 Sep 03; 69(18):5966-73.JO

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+Show Affiliations

Hayashi 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 J
No affiliation info available
Sumiya T
No affiliation info available
Hibino K
No affiliation info available
Shoji M
No affiliation info available

MeSH

AldehydesCatalysisKetonesModels, MolecularMolecular StructureNitroso CompoundsOxygenProlineStereoisomerismTemperature

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15373480

Citation

Hayashi, Yujiro, et al. "Direct Proline-catalyzed Asymmetric Alpha-aminoxylation of Aldehydes and Ketones." The Journal of Organic Chemistry, vol. 69, no. 18, 2004, pp. 5966-73.
Hayashi Y, Yamaguchi J, Sumiya T, et al. Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones. J Org Chem. 2004;69(18):5966-73.
Hayashi, Y., Yamaguchi, J., Sumiya, T., Hibino, K., & Shoji, M. (2004). Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones. The Journal of Organic Chemistry, 69(18), 5966-73.
Hayashi Y, et al. Direct Proline-catalyzed Asymmetric Alpha-aminoxylation of Aldehydes and Ketones. J Org Chem. 2004 Sep 3;69(18):5966-73. PubMed PMID: 15373480.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct proline-catalyzed asymmetric alpha-aminoxylation of aldehydes and ketones. AU - Hayashi,Yujiro, AU - Yamaguchi,Junichiro, AU - Sumiya,Tatsunobu, AU - Hibino,Kazuhiro, AU - Shoji,Mitsuru, PY - 2004/9/18/pubmed PY - 2004/11/2/medline PY - 2004/9/18/entrez SP - 5966 EP - 73 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 18 N2 - 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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15373480/Direct_proline_catalyzed_asymmetric_alpha_aminoxylation_of_aldehydes_and_ketones_ DB - PRIME DP - Unbound Medicine ER -