71209-65-9Relevant academic research and scientific papers
Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation
Hardegger, Leo A.,Habegger, Jacqueline,Donohoe, Timothy J.
, p. 3222 - 3225 (2015)
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).
Synthesis and stereochemistry of β-aryl-β-haloacroleins: Useful intermediates for the preparation of (Z) and (E)-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides
Prim, Damien,Fuss, Alexia,Kirsch, Gilbert,Silva, Artur M. S.
, p. 1175 - 1180 (2007/10/03)
The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes
