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Short Paper | Regular issue | Vol 96, No. 5, 2018, pp.895-901
Published online, 19th April, 2018
DOI: 10.3987/COM-17-13846
Preparation of Chiral β-Enamino Esters from Methyl Propiolate: Synthesis of Chiral Methyl 1-Substituted 6-Oxo-1,4,5,6-tetrahydropyridine-3-carboxylates

Hugo Pilotzi, Dino Gnecco,* María L. Orea,* Jorge R. Juárez, David M. Aparicio, and Joel L. Terán

*Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC9, Complejo de Ciencias, C. U. 72570 Puebla, Pue., Mexico


An efficient procedure to prepare chiral β-enamino esters by reaction of methyl propiolate with chiral amines is described. Aza-annulation of these chiral β-enamino esters with acryloyl chloride afforded the corresponding chiral methyl 1-substituted 6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylates in good yield.