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Copper(I)-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Alkenes

Hiroaki Murayama, Kazunori Nagao, Hirohisa Ohmiya* and Masaya Sawamura*

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Email:,

H. Murayama, K. Nagao, H. Ohmiya, M. Sawamura, Org. Lett., 2015, 17, 2039-2041.

DOI: 10.1021/acs.orglett.5b00758

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A Cu(I)-Xantphos system catalyzed the intramolecular hydroalkoxylation of unactivated terminal alkenes, providing five- and six-membered cyclic ethers. A possible reaction pathway involves an addition of a Cu-O bond across the C-C double bond. The use of (R)-DTBM-SEGPHOS as ligand enabled an enantioselective reaction with moderate enantioselectivity.

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Key Words

tetrahydrofurans, tetrahydropyrans

ID: J54-Y2015