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Hydroxylamines as Oxygen Atom Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution

Hideto Miyabe, Kazumasa Yoshida, Masashige Yamauchi and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: takemotopharm.kyoto-u.ac.jp

H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto, J. Org. Chem., 2005, 70, 2148-2153.

DOI: 10.1021/jo047897t (free Supporting Information)


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Abstract

The oxygen atom of hydroxylamines having an N-electron-withdrawing substituent (also known as hydroxamic acids) acts as a reactive nucleophile in transition-metal-catalyzed allylic substitutions. The palladium-catalyzed O-allylic substitution of hydroxylamines with allylic carbonate afforded linear hydroxylamines, whereas branched hydroxylamines were observed in iridium-catalyzed reactions.


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Key Words

Allylic Substitutions, Hydroxylamines


ID: J42-Y2005-260