title: Switchable stereocontrolled divergent synthesis induced by aza-Michael addition of deactivated primary amines under acid catalysis.
abstract: Switchable tandem intramolecular aza-Michael/Michael and double aza-Michael reactions allow the oriented synthesis of highly functionalised cyclic skeletons. Conjugate addition of deactivated anilines triggers chemo- and stereo-divergent ring-closure reaction pathways with a striking selectivity depending on reaction conditions.
authors.affiliation: Université Paris-Sud, UMR 8076 BioCIS, LabEx LERMIT, Equipe de Chimie des Substances naturelles 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry (France).
authors.forename: Z
authors.initials: Z
authors.lastname: Amara
authors.forename: E
authors.initials: E
authors.lastname: Drège
authors.forename: C
authors.initials: C
authors.lastname: Troufflard
authors.forename: P
authors.initials: P
authors.lastname: Retailleau
authors.forename: M-E
authors.initials: ME
authors.lastname: Tran Huu-Dau
authors.forename: D
authors.initials: D
authors.lastname: Joseph
mesh_terms: D000143:Acids / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000143:Acids; D000588:Amines; D001372:Aza Compounds; D006844:Hydrocarbons, Cyclic
keywords: Michael addition; chemoselectivity; cyclization; diastereoselectivity; enones