908588-77-2Relevant academic research and scientific papers
Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions
Brunner, Bernhard,Stogaitis, Nicole,Lautens, Mark
, p. 3473 - 3476 (2006)
The application of vinyloxiranes, substituted with an electron-withdrawing group, as masked dienolates in vinylogous imino-aldol reactions was achieved. Under the reaction conditions highly substituted 1,2-dihydropyridines were obtained in moderate to good yields. Mechanistic studies indicate that the reaction proceeds via the formation of an (E)-amino-α,β-unsaturated aldehyde, followed by isomerization to the (Z)-isomer, cyclization, and elimination of a water molecule, leading to the formation of the 1,2-dihydropyridine.
