title: Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.
abstract: A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of substituted piperidines.
authors.affiliation: The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: Pavol
authors.initials: P
authors.lastname: Jakubec
authors.forename: Dane M
authors.initials: DM
authors.lastname: Cockfield
authors.forename: Madeleine
authors.initials: M
authors.lastname: Helliwell
authors.forename: James
authors.initials: J
authors.lastname: Raftery
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon