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Issue 18, 2010
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Gold(I)-catalysed alcohol additions to cyclopropenes

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Abstract

Gold(I)-catalysed addition of alcohols to 3,3-disubstituted cyclopropenes occurs in a highly regioselective and facile manner to produce alkyl tert-allylic ethers in good yields. The reaction is tolerant of sterically hindered substituents on the cyclopropene as well as primary and secondary alcohols as nucleophiles. In this full article, we report on the substrate scope and plausible mechanism, as well as the regioselectivity issues arising from subsequent gold(I)-catalysed isomerisation of tertiary to primary allylic ethers.

Graphical abstract: Gold(i)-catalysed alcohol additions to cyclopropenes

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Publication details

The article was received on 05 May 2010, accepted on 11 Jun 2010 and first published on 09 Jul 2010


Article type: Paper
DOI: 10.1039/C0OB00085J
Citation: Org. Biomol. Chem., 2010,8, 4090-4095
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    Gold(I)-catalysed alcohol additions to cyclopropenes

    M. S. Hadfield, J. T. Bauer, P. E. Glen and A. Lee, Org. Biomol. Chem., 2010, 8, 4090
    DOI: 10.1039/C0OB00085J

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