Gold(I)-catalysed alcohol additions to cyclopropenes

Organic & Biomolecular Chemistry
Maximillian S HadfieldAi-Lan Lee

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.

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Citations

Jul 28, 2011·Journal of the American Chemical Society·Jingwei LiDaesung Lee
Jul 31, 2012·The Journal of Organic Chemistry·Richard J MuddAi-Lan Lee
Aug 28, 2013·The Journal of Organic Chemistry·Nasir Ahmad RajabiAlireza Ariafard
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Aug 2, 2011·Beilstein Journal of Organic Chemistry·Frédéric MiegeJanine Cossy
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Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
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Dec 23, 2011·Chemical Society Reviews·Bei-Li LuMin Shi
Jul 7, 2019·Angewandte Chemie·Jie ChenTeck-Peng Loh
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Mar 20, 2015·Chemistry : a European Journal·Yahui WangAntonio M Echavarren
May 9, 2012·Organic & Biomolecular Chemistry·Maximillian S HadfieldAshley M Watson
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Mar 13, 2015·Accounts of Chemical Research·Alexis ArchambeauJanine Cossy
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