Journal
ORGANIC LETTERS
Volume 17, Issue 13, Pages 3222-3225Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01312
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Funding
- Swiss National Science Foundation
- Marie Curie actions fellowships
- Berrow Foundation Lord Florey scholarship
- EPSRC (Established Career Fellowship)
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A, novel methodology for the synthesis of highly substituted pyridines based on the palladium-catalyzed enolate alpha-alkenylation of ketones is presented; the formation of aromatic compounds: is: a new direction for this catalytic C-C bond forming reaction. In the, key step, a protected beta-haloalkenylaldehyde participates in alpha-alkenylution with a ketone to afford a 1,5-dicarbonyl surrogate,, which then undergoes cyclitation/double elimination to the corresponding pyridine:product, all in one pot., The beta-haloalkenylaldehyde starting materials can be obtained from the corresponding methylene ketone via Vilsmeier haloformylation. Using this concise route, a variety, of highly substituted pyridines were synthesized in three steps from commercially available compounds.
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