title: Synthesis of enantiomerically enriched propargylamines by copper-catalyzed addition of alkynes to enamines.
abstract: The first copper(I) bromide/Quinap-catalyzed synthesis of enantiomerically enriched propargylamines by addition of alkynes to enamines is reported. Various functionalized terminal alkynes add smoothly to Nprotected enamines to afford the corresponding amines in good to high yields and moderate to good enantiomeric excesses. The influence of the metal salt, the ligand, and the protecting group on the conversion, the reaction rate, and the stereoselectivity of the reaction are investigated. The scope of the reaction and further transformations of the resulting propargylamines (deprotection, Pauson-Khand reaction) are also described.
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität, Munich, Germany.
authors.forename: Christopher
authors.initials: C
authors.lastname: Koradin
authors.forename: Nina
authors.initials: N
authors.lastname: Gommermann
authors.forename: Kurt
authors.initials: K
authors.lastname: Polborn
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D011437:Propylamines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000588:Amines; D011437:Propylamines; C009054:propargylamine; D003300:Copper; D010293:Pargyline