ArticleAngewandte Chemie (International ed. in English)2022
Diastereo- and Enantioselective Inverse-Electron-Demand Diels-Alder Cycloaddition between 2-Pyrones and Acyclic Enol Ethers.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 28 citations in OpenAlex.
- Asymmetric Catalysis: Recent Advances toward a More Sustainable Synthesis.ACS central science · 2026Review
- Natural Product Synthesis: The Endless Quest for Unreachable Perfection.ACS organic & inorganic Au · 2023Review
- Enantioselective and collective total synthesis of pentacyclic 19-Chemical science · 2023Article
- Diastereo- and Enantioselective Inverse-Electron-Demand Diels-Alder Cycloaddition between 2-Pyrones and Acyclic Enol Ethers.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors at 2 institutions in 2 countries.
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Abstract
A broadly applicable diastereo- and enantioselective inverse-electron-demand Diels-Alder reaction of 2-pyrones and acyclic enol ethers is reported herein. Using a copper(II)-BOX catalytic system, bridged bicyclic lactones are obtained in very high yields (up to 99 % yield) and enantioselectivities (up to 99 % ee) from diversely substituted 2-pyrones and acyclic enol ethers. Mechanistic experiments as well as DFT calculations indicate the occurrence of a stepwise mechanism. The synthetic potential of the bridged bicyclic lactones is showcased by the enantioselective synthesis of polyfunctional cyclohexenes and cyclohexadienes, as well as a carbasugar unit.
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