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Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers
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| Zeitschriftentitel: | Angewandte Chemie |
|---|---|
| Personen und Körperschaften: | , , , , |
| In: | Angewandte Chemie, 134, 2022, 42 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
|
| Schlagwörter: |
| author_facet |
Huang, Guanghao Guillot, Régis Kouklovsky, Cyrille Maryasin, Boris de la Torre, Aurélien Huang, Guanghao Guillot, Régis Kouklovsky, Cyrille Maryasin, Boris de la Torre, Aurélien |
|---|---|
| author |
Huang, Guanghao Guillot, Régis Kouklovsky, Cyrille Maryasin, Boris de la Torre, Aurélien |
| spellingShingle |
Huang, Guanghao Guillot, Régis Kouklovsky, Cyrille Maryasin, Boris de la Torre, Aurélien Angewandte Chemie Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers General Medicine |
| author_sort |
huang, guanghao |
| spelling |
Huang, Guanghao Guillot, Régis Kouklovsky, Cyrille Maryasin, Boris de la Torre, Aurélien 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.202208185 <jats:title>Abstract</jats:title><jats:p>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.</jats:p> Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers Angewandte Chemie |
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| title |
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_unstemmed |
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_full |
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_fullStr |
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_full_unstemmed |
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_short |
Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_sort |
diastereo‐ and enantioselective inverse‐electron‐demand diels–alder cycloaddition between 2‐pyrones and acyclic enol ethers |
| topic |
General Medicine |
| url |
http://dx.doi.org/10.1002/ange.202208185 |
| publishDate |
2022 |
| physical |
|
| description |
<jats:title>Abstract</jats:title><jats:p>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.</jats:p> |
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| author | Huang, Guanghao, Guillot, Régis, Kouklovsky, Cyrille, Maryasin, Boris, de la Torre, Aurélien |
| author_facet | Huang, Guanghao, Guillot, Régis, Kouklovsky, Cyrille, Maryasin, Boris, de la Torre, Aurélien, Huang, Guanghao, Guillot, Régis, Kouklovsky, Cyrille, Maryasin, Boris, de la Torre, Aurélien |
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| description | <jats:title>Abstract</jats:title><jats:p>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.</jats:p> |
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| institution | DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14 |
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| spelling | Huang, Guanghao Guillot, Régis Kouklovsky, Cyrille Maryasin, Boris de la Torre, Aurélien 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.202208185 <jats:title>Abstract</jats:title><jats:p>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.</jats:p> Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers Angewandte Chemie |
| spellingShingle | Huang, Guanghao, Guillot, Régis, Kouklovsky, Cyrille, Maryasin, Boris, de la Torre, Aurélien, Angewandte Chemie, Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers, General Medicine |
| title | Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_full | Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_fullStr | Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_full_unstemmed | Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_short | Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| title_sort | diastereo‐ and enantioselective inverse‐electron‐demand diels–alder cycloaddition between 2‐pyrones and acyclic enol ethers |
| title_unstemmed | Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers |
| topic | General Medicine |
| url | http://dx.doi.org/10.1002/ange.202208185 |