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

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

doi:10.1021/jo049338s

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

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

SCI - Chemistry

Tokyo University of Science

Research output: Contribution to journal › Article › peer-review

149 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 language	English
Pages (from-to)	5966-5973
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	69
Issue number	18
DOIs	https://doi.org/10.1021/jo049338s
Publication status	Published - 2004 Sept 3

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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.",

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AU - Hayashi, Yujiro

AU - Yamaguchi, Junichiro

AU - Sumiya, Tatsunobu

AU - Hibino, Kazuhiro

AU - Shoji, Mitsuru

PY - 2004/9/3

Y1 - 2004/9/3

N2 - 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.

AB - 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.

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

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