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Copper-Catalyzed Regioselective Ring-Opening Hydroamination of Methylenecyclopropanes

Daiki Nishikawa, Ryosuke Sakae, Yuya Miki, Koji Hirano* and Masahiro Miura*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: k_hiranochem.eng.osaka-u.ac.jp, miurachem.eng.osaka-u.ac.jp

D. Nishikawa, R. Sakae, Y. Miki, K. Hirano, M. Miura, J. Org. Chem., 2016, 81, 12128-12134.

DOI: 10.1021/acs.joc.6b02483 (free Supporting Information)



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Abstract

A copper-catalyzed ring-opening hydroamination of methylenecyclopropanes with polymethylhydrosiloxane and O-benzoylhydroxylamines provides homoallylamines in very good yields. The cyclopropane C-C bond cleavage occurs selectively at the more congested proximal position.


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Key Words

homoallylic amines, PMHS


ID: J42-Y2016