title: Gold(I)-catalyzed 1,4- and/or 1,5-heteroaryl migration reactions through regiocontrolled cyclizations.
abstract: Gold(I)-catalyzed regioselective cycloisomerizations of furan-ynes have been described. The reaction provides a concise access to stereodefined trisubstituted alkenes by endo cyclization with concomitant 1,5-migration of the furanyl group in the presence of unactivated 3 Å molecular sieves. In the absence of molecular sieves, indene products are generated by exo cyclization, followed by 1,4-furanyl migration/cyclization. The scope for 1,5-migrations can be extended to other heterocycles, such as benzofurans, thiophenes, and pyrroles.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P. R. China); Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 (P. R. China).
authors.forename: Chengyu
authors.initials: C
authors.lastname: Wang
authors.forename: Xin
authors.initials: X
authors.lastname: Xie
authors.forename: Jun
authors.initials: J
authors.lastname: Liu
authors.forename: Yuanhong
authors.initials: Y
authors.lastname: Liu
authors.forename: Yuxue
authors.initials: Y
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D005663:Furans; D006046:Gold; C039281:furan
keywords: alkenes; furans; gold catalysis; migration; stereoselectivity