ArticleAngewandte Chemie (International ed. in English)2016
Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade.
Article in Angewandte Chemie (International ed. in English), 2016. 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, 17 citations in OpenAlex.
- What is a Cross-Coupling? An Argument for a Universal Definition.Tetrahedron · 2023Article
- Progress toward the De Novo Asymmetric Synthesis of Euphanes.Organic letters · 2022Article
- Stereoselective synthesis of pentasubstituted 1,3-dienesChemical science · 2020Article
- Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.ACS catalysis · 2019Article
- Modern applications of low-valent early transition metals in synthesis and catalysis.Nature reviews. Chemistry · 2019Article
- Synthesis of Highly Oxygenated Carbocycles by Stereoselective Coupling of Alkynes to 1,3- and 1,4-Dicarbonyl Systems.Journal of the American Chemical Society · 2017Article
- The Development of Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling Chemistry.Israel journal of chemistry · 2017Article
- A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.ARKIVOC : free online journal of organic chemistryArticle
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Authors and funding
2 authors at 1 institution in 1 country.
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Abstract
A convergent coupling reaction is described that enables the stereoselective construction of angularly substituted trans-fused decalins from acyclic precursors. The process builds on our alkoxide-directed titanium-mediated alkyne-alkyne coupling and employs a 1,7-enyne coupling partner. Overall, the reaction is thought to proceed through initial formation of a tetrasusbstituted metallacyclopentadiene, stereoselective intramolecular [4+2] cycloaddition, elimination, isomerization, and regio- and stereoselective protonation. Distinct from our early studies directed at the synthesis of trans-fused hydrindanes, the current annulative coupling reveals an important effect of TMSCl in controlling the final protonation-the event that establishes the stereochemistry of the ring fusion.
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