Copper(I)-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Alkenes

A Cu­(I)–Xantphos system catalyzed the intramolecular hydroalkoxylation of unactivated terminal alkenes, giving five- and six-membered ring ethers. This system is applicable to both primary and secondary alcohols. A reaction pathway involving the addition of the Cu–O bond across the C–C double bond...

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Bibliographic Details
Published in:Organic letters 2015-05, Vol.17 (9), p.2039-2041
Main Authors: Murayama, Hiroaki, Nagao, Kazunori, Ohmiya, Hirohisa, Sawamura, Masaya
Format: Article
Language:English
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Summary:A Cu­(I)–Xantphos system catalyzed the intramolecular hydroalkoxylation of unactivated terminal alkenes, giving five- and six-membered ring ethers. This system is applicable to both primary and secondary alcohols. A reaction pathway involving the addition of the Cu–O bond across the C–C double bond is proposed. A chiral Cu­(I) catalyst system based on the (R)-DTBM-SEGPHOS ligand promoted enantioselective reaction with moderate enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00758