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

薬科学科

研究成果: Article › 査読

148 被引用数 (Scopus)

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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.

本文言語	English
ページ（範囲）	5966-5973
ページ数	8
ジャーナル	Journal of Organic Chemistry
巻	69
号	18
DOI	https://doi.org/10.1021/jo049338s
出版ステータス	Published - 2004 9月 3

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有機化学

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10.1021/jo049338s

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AU - Hayashi, Yujiro

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AU - Sumiya, Tatsunobu

AU - Hibino, Kazuhiro

AU - Shoji, Mitsuru

PY - 2004/9/3

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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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