ArticleAngewandte Chemie (International ed. in English)2018
Copper-Catalyzed Formal [4+2] Cycloaddition of Enoldiazoimides with Sulfur Ylides.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Synthesis ofChemical communications (Cambridge, England) · 2025Article
- Organothianthrenium salts: synthesis and utilization.Chemical science · 2022Review
- Oxygenated Cyclopentenones via the Pauson-Khand Reaction of Silyl Enol Ether Substrates.Organic letters · 2022Article
- Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.Chemical reviews · 2019Article
- Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.Organic & biomolecular chemistry · 2019Review
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6 authors.
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Abstract
Enoldiazoimides, a new subclass of enoldiazo compounds, generate enol-substituted carbonyl ylides whose reactions with sulfur ylides enable an unprecedented formal [4+2] cycloaddition. The resulting multifunctionalized indolizidinones, which incorporate sulfur, are formed in good yields under mild reaction conditions. The uniqueness of this transformation stems from the role of the silyl-protected enol, since the corresponding acetyldiazoimide failed to provide any cross-products in metal-catalyzed reactions with sulfur ylides. This copper-catalyzed cycloaddition is initiated with the generation of enol-substituted carbonyl ylides and sulfur ylides from enoldiazoimides and sulfonium salts, respectively, and proceeds through stepwise six-membered ring formation, C-O and C-S bond cleavage, and silyl and acetyl group migration.
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