Dynamic kinetic resolution and desymmetrization processes: a straightforward methodology for the enantioselective synthesis of piperidines.
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.
Amat
Mercedes
M
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain. amat@ub.edu
Bassas
Oriol
O
Llor
Núria
N
Cantó
Margalida
M
Pérez
Maria
M
Molins
Elies
E
Bosch
Joan
J
D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007700:Kinetics; D007769:Lactams / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004983:Ethanolamines; D007769:Lactams; D010880:Piperidines; C005332:N-phenylethanolamine; D005998:Glycine