Issue 18, 2010
From the journal:

Organic & Biomolecular Chemistry

Gold(i)-catalysed alcohol additions to cyclopropenes†

Maximillian S. Hadfield,a   Jürgen T. Bauer,a   Pauline E. Glena  and  Ai-Lan Lee*a  

* Corresponding authors

a School of Engineering and Physical Sciences, Chemistry–William H. Perkin Building, Heriot-Watt University, Edinburgh, UK
E-mail: A.Lee@hw.ac.uk
Tel: +44(0)131-4518030

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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Article information

DOI
https://doi.org/10.1039/C0OB00085J
Article type
Paper
Submitted
05 May 2010
Accepted
11 Jun 2010
First published
09 Jul 2010

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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