title: Conjugate addition of organocuprates to chiral bicyclic delta-lactams. Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines.
abstract: [reaction: see text] Chiral nonracemic bicyclic lactam 3, easily accessible by cyclodehydration of (R)-phenylglycinol and racemic methyl 4-formylhexanoate, was converted to the unsaturated lactams 5, which undergo the stereoselective conjugate addition of lower order cyanocuprates to ultimately lead to enantiopure cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Spain. amat@farmacia.far.ub.es
authors.forename: M
authors.initials: M
authors.lastname: Amat
authors.forename: M
authors.initials: M
authors.lastname: Pérez
authors.forename: N
authors.initials: N
authors.lastname: Llor
authors.forename: J
authors.initials: J
authors.lastname: Bosch
authors.forename: E
authors.initials: E
authors.lastname: Lago
authors.forename: E
authors.initials: E
authors.lastname: Molins
mesh_terms: D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006574:Heterocyclic Compounds, 2-Ring; D007769:Lactams; D010880:Piperidines