title: Base-catalyzed intramolecular hydroamination of conjugated enynes.
abstract: A de novo intramolecular hydroamination of conjugated enynes was developed using commercially available n-BuLi as a precatalyst. This hydroamination reaction successfully afforded allenyl-substituted pyrrolidines with up to 95% yield. One of the resulting allenyl pyrrolidines was converted to the natural products irniine and irnidine in three steps.
authors.affiliation: The School of Pharmacy and Department of Chemistry, University of Wisconsin, 777 Highland Avenue, Madison, Wisconsin 53705-2222, USA.
authors.forename: Wen
authors.initials: W
authors.lastname: Zhang
authors.forename: Jenny B
authors.initials: JB
authors.lastname: Werness
authors.forename: Weiping
authors.initials: W
authors.lastname: Tang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D009942:Organometallic Compounds; D011759:Pyrrolidines; C434823:n-butyllithium