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Short Paper | Regular issue | Vol 91, No. 5, 2015, pp.1042-1047
Published online, 14th April, 2015
DOI: 10.3987/COM-15-13206
Diasterospecific Etherification and Diasteroselective Monobromination of (R)-()-1-(2-Hydroxy-1-phenylethyl)-3,4-dihydropyridin-2(1H)-one

Anna Vargas, María L. Orea,* Joel L. Terán, David M. Aparicio, Jorge R. Juárez, Raúl G. Enríquez, and Dino Gnecco

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


A one pot diasterospecific etherification and diasteroselective monobromination with bromine or N-bromosuccinimide (NBS) of the endocyclic enamide (R)-()-1-(2-hydroxy-1-phenylethyl)-3,4-dihydropyridin-2(1H)-one 1 is described. The enantiopure 8-bromo-3-phenyltetrahydro-2H-oxazolo[3,2-a]pyridin-5(3H)-ones trans-2 and cis-2 were obtained in good yield, fully characterized and its relative stereochemistry was unambiguously assigned via single-crystal X-ray structure.