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Tandem Palladium-Catalyzed 6- exo- dig Oxocyclization Coupling of δ-Acetylenic β-Ketoesters with Aryl Bromides and Chlorides: Route to Substituted Dihydropyrans.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2018 Oct 19; Vol. 83 (20), pp. 12887-12896. Date of Electronic Publication: 2018 Sep 28. - Publication Year :
- 2018
-
Abstract
- We report an efficient and functional group-tolerant method for the synthesis of substituted dihydropyrans, based on tandem Pd-catalyzed cyclization/coupling of δ-acetylenic β-ketoesters with aryl halides. The reaction proceeds cleanly through 6- exo-dig oxocyclizaton mode, delivering products with very good yields and complete control of regio- and stereoselectivity. Due to mild conditions, the transformation offers exceptional tolerance of functionalities, including NHR, formyl, enolizable ketone, free OH and NH <subscript>2</subscript> groups, as well as a range of N-heterocyclic moieties of potential biological relevance.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 83
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30204434
- Full Text :
- https://doi.org/10.1021/acs.joc.8b01832