title: Dynamic kinetic resolution and desymmetrization processes: a straightforward methodology for the enantioselective synthesis of piperidines.
abstract: A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)-phenylglycinol or other amino alcohols with racemic or prochiral delta-oxo (di)acid derivatives in highly stereoselective processes involving dynamic kinetic resolution and/or desymmetrization of diastereotopic or enantiotopic ester groups.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain. amat@ub.edu
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.forename: Oriol
authors.initials: O
authors.lastname: Bassas
authors.forename: Núria
authors.initials: N
authors.lastname: Llor
authors.forename: Margalida
authors.initials: M
authors.lastname: Cantó
authors.forename: Maria
authors.initials: M
authors.lastname: Pérez
authors.forename: Elies
authors.initials: E
authors.lastname: Molins
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007700:Kinetics; D007769:Lactams / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004983:Ethanolamines; D007769:Lactams; D010880:Piperidines; C005332:N-phenylethanolamine; D005998:Glycine