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Short Paper | Regular issue | Vol 89, No. 3, 2014, pp.725-729
Published online, 4th February, 2014
DOI: 10.3987/COM-13-12911
Oxidation and Aromatization of the Enantiopure Piperidine Derived from (R)-(-)-2-Phenylglycinol to (1’R)-(-)-1-(2’-Hydroxy-1’-phenylethyl)-1H-pyridin-2-one

Alejandro Castro, Oscar Romero, Joel L. Terán, Dino Gnecco, Laura Orea, Angel Mendoza, and Jorge R. Juárez*

*Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. 103G, 103H, 72570, Mexico

Abstract

An efficient oxidation of enantiopure piperidine 1 with bromine in acetic acid to generate the corresponding enantiopure (R)-3,3-dibromo-1-(2’-hydroxy-1’-phenylethyl)piperidin-2-one 2 is described. Then, aromatization of compound 2 to give enantiopure pyridin-2-one 3 in 71% overall yield is presented.