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
Externally publishedYes

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Ketones
Proline
Aldehydes
Enantioselectivity
Oxygen
Temperature
nitrosobenzene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones. / Hayashi, Yujiro; Yamaguchi, Junichiro; Sumiya, Tatsunobu; Hibino, Kazuhiro; Shoji, Mitsuru.

In: Journal of Organic Chemistry, Vol. 69, No. 18, 03.09.2004, p. 5966-5973.

Research output: Contribution to journalArticle

Hayashi, Yujiro ; Yamaguchi, Junichiro ; Sumiya, Tatsunobu ; Hibino, Kazuhiro ; Shoji, Mitsuru. / Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 18. pp. 5966-5973.
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