1089296-34-3Relevant academic research and scientific papers
Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation
Hardegger, Leo A.,Habegger, Jacqueline,Donohoe, Timothy J.
supporting information, p. 3222 - 3225 (2015/07/15)
A novel methodology for the synthesis of highly substituted pyridines based on the palladium-catalyzed enolate α-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 β-haloalkenylaldehyde participates in α-alkenylation with a ketone to afford a 1,5-dicarbonyl surrogate, which then undergoes cyclization/double elimination to the corresponding pyridine product, all in one pot. The β-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. (Chemical Equation Presented).
