Abstract
During the last decade, gold-catalyzed reactions have become a tour de force in organic synthesis. Recently, the gold-, Brønsted acid- or Lewis acid-catalyzed oxygen transfer from carbonyl to carbon–carbon triple bond, the so-called alkyne–carbonyl metathesis, has attracted much attention because this atom economical transformation generates α,β-unsaturated carbonyl derivatives which are of great interest in synthetic organic chemistry. This mini-review focuses on the most recent achievements on gold-catalyzed oxygen transfer reactions of tethered alkynones, diynes or alkynyl epoxides to cyclic enones. The corresponding mechanisms for the transformations are also discussed.
Highlights
During the early years of this century, organic chemists became aware that gold salts or complexes were highly active catalysts in homogeneous catalysis because of the strong π- and σ-electrophilicity of gold [28-33]
The number of new gold-catalyzed reactions reported in the literature has increased substantially and gold catalysis has become one of the hottest research fields in synthetic organic chemistry [34-42]
Due to their unique alkynophilicity, gold catalysts are especially suited to the activation of carbon–carbon triple bonds
Summary
Address: Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, KY 40292, USA This article is part of the Thematic Series "Gold catalysis in organic synthesis". Keywords: alkyne–carbonyl metathesis; cyclic enones; gold-catalyzed; oxonium; oxygen transfer
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