title: Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.
abstract: A 1:1 mixture of (1)AuCl [1 = P(t-Bu)(2)o-biphenyl] and AgSbF(6) catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.
authors.affiliation: Duke University, Department of Chemistry, French Family Science Center, Durham, North Carolina 27708-0346, United States.
authors.forename: Paramita
authors.initials: P
authors.lastname: Mukherjee
authors.forename: Ross A
authors.initials: RA
authors.lastname: Widenhoefer
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D010880:Piperidines; D020005:Propanols; D011759:Pyrrolidines; C006463:allyl alcohol; D006046:Gold