title: Stereoselective conjugate addition reactions to phenylglycinol-derived, unsaturated oxazolopiperidone lactams.
abstract: Phenylglycinol-derived, unsaturated oxazolopiperidone lactams are extremely useful building blocks that undergo stereoselective conjugate addition reactions with organocuprates, enolates, and sulfur-stabilized anions, allowing the stereocontrolled introduction of substituents at the piperidine 4-position. The factors governing the exo- or endo-facial selectivity are discussed. The methodology can be used for the preparation of a variety of enantiopure piperidines, including pharmaceuticals, alkaloids precursors, piperidine-fused derivatives, as well as complex piperidine-containing natural products.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Insitute of Biomedicine (IBUB), 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: Maria
authors.initials: M
authors.lastname: Pérez
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D001688:Biological Products / Q000737:chemistry; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004983:Ethanolamines; D007769:Lactams; D010880:Piperidines; C005332:N-phenylethanolamine; D005998:Glycine