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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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Supplementary files

Article information


Submitted
05 May 2010
Accepted
11 Jun 2010
First published
09 Jul 2010

Org. Biomol. Chem., 2010,8, 4090-4095
Article type
Paper

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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