ArticleChemistry (Weinheim an der Bergstrasse, Germany)2014
1,2-N-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Divergent Synthesis of Polycyclic N‑Heterocycles via Controllable Cyclization of Divinylallenes Catalyzed by Copper and Gold.JACS Au · 2025Article
- Mechanistic Studies on the Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides to Indenes.ACS omega · 2024Article
- Cu(i) catalysis for selective condensation/bicycloaromatization of two different arylalkynes: direct and general construction of functionalized C-N axial biaryl compounds.Chemical science · 2021Article
- Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.Nature communications · 2019Article
- A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides.Angewandte Chemie (International ed. in English) · 2015Article
- Gold-catalyzed tandem reactions of amide-aldehyde-alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles.Chemical science · 2015Article
- Ynamide carbopalladation: a flexible route to mono-, bi- and tricyclic azacycles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
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Abstract
Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.
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