An efficient synthesis of (S)- and (R)-3-hydroxypiperidin-2-ones from methyl 5-nitro-2-oxopentanoate is described. A one-pot enzyme catalysed hydrolysis of the ester and reduction of the ketone gave enantiopure 2- hydroxy-5-nitropentanoic acids which on esterification, catalytic hydrogenation over a platinum(IV) oxide catalyst and intramolecular: cyclisation gave the target compounds in 93% overall yield and >99% ee.
Gibbs, G., Hateley, M. J., McLaren, L., Welham, M., & Willis, C. L. (1999). Enantioselective synthesis of 3-hydroxypiperidin-2-ones. Tetrahedron Letters, 40(5), 1069–1072. https://doi.org/10.1016/S0040-4039(99)80114-2