title: Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams.
abstract: The stereochemical outcome of the enolate dialkylation of simple phenylglycinol-derived oxazolopiperidone lactams is studied. High stereoselectivities in the generation of the quaternary stereocenter are obtained by the appropriate choice of both the configuration of the starting lactam and the order of introduction of the substituents. The usefulness of the methodology is illustrated by the conversion of some of the dialkylated lactams into known synthetic precursors of alkaloids and by the total synthesis of (-)-quebrachamine.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain. amat@ub.edu
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.forename: Oscar
authors.initials: O
authors.lastname: Lozano
authors.forename: Carmen
authors.initials: C
authors.lastname: Escolano
authors.forename: Elies
authors.initials: E
authors.lastname: Molins
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000478:Alkylation; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis; D007769:Lactams / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D010881:Piperidones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004983:Ethanolamines; D026121:Indole Alkaloids; D007769:Lactams; D010080:Oxazoles; D010880:Piperidines; D010881:Piperidones; C005332:N-phenylethanolamine; C091897:quebrachamine; D005998:Glycine