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: takemoto
pharm.kyoto-u.ac.jp
H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto, J. Org. Chem., 2005, 70, 2148-2153.
DOI: 10.1021/jo047897t
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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
