title: Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines.
abstract: A novel gold-catalyzed divergent sysnthesis of furans and pyrroles employing readily available homopropargylic aldehydes and imines have been developed. The regiochemical outcome of this reaction is dependent on the substituent on the terminal alkyne of substrate. Thus, substrates possessing alkyl and aryl substituent at the alkyne moiety produce 2,3,5-substituted furans and pyrroles via a migratory cycloisomerizaton reaction. Whereas, their silicon analogues are capable to undergo a double migratory process leading to 2,3,4-substituted heterocycles.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL 60607-7061, United States.
authors.forename: Roohollah Kazem
authors.initials: RK
authors.lastname: Shiroodi
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL 60607-7061, United States.
authors.forename: Claudia I Rivera
authors.initials: CI
authors.lastname: Vera
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL 60607-7061, United States.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Dudnik
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL 60607-7061, United States.
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
keywords: Cycloisomerization; Double migration; Gold catalyst; Heterocycles; Silicon migration