Enantioselective synthesis of 3-hydroxypiperidin-2-ones

Abstract

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.