Gold(i)-catalysed alcohol additions to cyclopropenes

Maximillian S. Hadfield, Jürgen T. Bauer, Pauline E. Glen, Ai L. Lee

Research output: Contribution to journalArticle

63 Citations (Scopus)

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. © 2010 The Royal Society of Chemistry.

Original languageEnglish
Pages (from-to)4090-4095
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number18
DOIs
Publication statusPublished - 21 Sep 2010

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