Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants.
A novel palladium(II)-catalyzed oxy-carbopalladation process was developed allowing for the orchestrated union of hydroxy ynones with ethyl acrylate, two electron-deficient reactants. With beta-hydroxy ynones, this cascade Wacker-Heck process gave access to highly functionalized tri- or tetrasubstit...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2006
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| _version_ | 1826286799939436544 |
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| author | Silva, F Reiter, M Mills-Webb, R Sawicki, M Klär, D Bensel, N Wagner, A Gouverneur, V |
| author_facet | Silva, F Reiter, M Mills-Webb, R Sawicki, M Klär, D Bensel, N Wagner, A Gouverneur, V |
| author_sort | Silva, F |
| collection | OXFORD |
| description | A novel palladium(II)-catalyzed oxy-carbopalladation process was developed allowing for the orchestrated union of hydroxy ynones with ethyl acrylate, two electron-deficient reactants. With beta-hydroxy ynones, this cascade Wacker-Heck process gave access to highly functionalized tri- or tetrasubstituted dihydropyranones featuring an unusual dienic system. For diastereomerically pure and for enantioenriched beta-hydroxyynones, these reactions proceed without affecting the stereochemical integrity of the existing stereocenters. In addition, tetrasubstituted furanones can be prepared when alpha-hydroxyynones and ethyl acrylate are used as starting materials. The dihydropyranones and furanones obtained upon cyclization are novel compounds, but structurally related carbohydrate derivatives featuring a similar dienic system have been used as starting materials for the construction of polyannulated products, suggesting that these cascade Pd(II)-mediated oxidative heterocyclizations are of value for various synthetic applications. |
| first_indexed | 2024-03-07T01:49:06Z |
| format | Journal article |
| id | oxford-uuid:997403f4-d9c4-446d-a023-e1068cddc201 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:49:06Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:997403f4-d9c4-446d-a023-e1068cddc2012022-03-27T00:14:24ZPd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:997403f4-d9c4-446d-a023-e1068cddc201EnglishSymplectic Elements at Oxford2006Silva, FReiter, MMills-Webb, RSawicki, MKlär, DBensel, NWagner, AGouverneur, VA novel palladium(II)-catalyzed oxy-carbopalladation process was developed allowing for the orchestrated union of hydroxy ynones with ethyl acrylate, two electron-deficient reactants. With beta-hydroxy ynones, this cascade Wacker-Heck process gave access to highly functionalized tri- or tetrasubstituted dihydropyranones featuring an unusual dienic system. For diastereomerically pure and for enantioenriched beta-hydroxyynones, these reactions proceed without affecting the stereochemical integrity of the existing stereocenters. In addition, tetrasubstituted furanones can be prepared when alpha-hydroxyynones and ethyl acrylate are used as starting materials. The dihydropyranones and furanones obtained upon cyclization are novel compounds, but structurally related carbohydrate derivatives featuring a similar dienic system have been used as starting materials for the construction of polyannulated products, suggesting that these cascade Pd(II)-mediated oxidative heterocyclizations are of value for various synthetic applications. |
| spellingShingle | Silva, F Reiter, M Mills-Webb, R Sawicki, M Klär, D Bensel, N Wagner, A Gouverneur, V Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants. |
| title | Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants. |
| title_full | Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants. |
| title_fullStr | Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants. |
| title_full_unstemmed | Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants. |
| title_short | Pd(II)-catalyzed cascade Wacker-Heck reaction: chemoselective coupling of two electron-deficient reactants. |
| title_sort | pd ii catalyzed cascade wacker heck reaction chemoselective coupling of two electron deficient reactants |
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