Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones

Yujiro Hayashi, Junichiro Yamaguchi, Tatsunobu Sumiya, Kazuhiro Hibino, Mitsuru Shoji

Research output: Contribution to journalArticle

139 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5966-5973
Number of pages8
JournalJournal of Organic Chemistry
Volume69
Issue number18
DOIs
Publication statusPublished - 2004 Sep 3

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones'. Together they form a unique fingerprint.

  • Cite this

    Hayashi, Y., Yamaguchi, J., Sumiya, T., Hibino, K., & Shoji, M. (2004). Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones. Journal of Organic Chemistry, 69(18), 5966-5973. https://doi.org/10.1021/jo049338s