ArticleAngewandte Chemie (International ed. in English)2020
Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Tunable Endo/Exo Selectivity in Direct Catalytic Asymmetric 1,3-Dipolar Cycloadditions with Polyfunctional Lewis Acid / Azolium-Aryloxide Catalysts.Angewandte Chemie (International ed. in English) · 2025Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Peptide-Catalyzed Stereoselective Conjugate Addition Reaction of Aldehydes to C-Substituted Maleimides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Highly Active Cooperative Lewis Acid-Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones.Angewandte Chemie (International ed. in English) · 2021Article
- A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones.RSC advances · 2021Article
- Enantioselective transition metal catalysis directed by chiral cations.Chemical science · 2020Review
- Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Diels-Alder reactions have become established as one of the most effective ways to prepare stereochemically complex six-membered rings. Different catalysis concepts have been reported, including dienophile activation by Lewis acids or H-bond donors and diene activation by bases. Herein we report a new concept, in which an acidic prodiene is acidified by a Lewis acid to facilitate deprotonation by an imidazolium-aryloxide entity within a polyfunctional catalyst. A metal dienolate is thus formed, while an imidazolium-ArOH moiety probably forms hydrogen bonds with the dienophile. The catalyst type, readily prepared in few steps in high overall yield, was applied to 3-hydroxy-2-pyrone and 3-hydroxy-2-pyridone as well as cyclopentenone prodienes. Maleimide, maleic anhydride, and nitroolefin dienophiles were employed. Kinetic, spectroscopic, and control experiments support a cooperative mode of action. High enantioselectivity was observed even with unprecedented TONs of up to 3680.
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