Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 20, Pages 12887-12896Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01832
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Funding
- Polish National Science Centre [DEC-2016/22/E/ST5/00537]
- Polish Ministry of Science and Higher Education
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We report an efficient and functional group-tolerant method for the synthesis of substituted dihydropyrans, based on tandem Pd-catalyzed cyclization/coupling of S-acetylenic beta-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 NH2 groups, as well as a range of N-heterocyclic moieties of potential biological relevance.
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