title: One-pot protocol to functionalized benzopyrrolizidine catalyzed successively by Rh2(OAc)4 and Cu(OTf)2: a transition metal-Lewis acid catalysis relay.
abstract: 4-N-allylarylpropylamino-1-sulfonyl triazoles are converted to structurally unique benzopyrrolizidinyl sulfonamides in a one-pot operation. Intramolecular capture of rhodium carbene with arylamino nitrogen gives rise to the formation of an ammonium ylide immediate. A [2,3]- or [1,2]-rearrangement occurs to give a 2-allylpyrrolidinyl-2-carbimine intermediate which undergoes Cu(OTf)2 catalyzed aza-Friedel-Crafts cyclization to finish a highly functionalized tricyclic system decorated with a synthetically difficult quaternary carbon center, a sulfonamide group, and an allyl segment.
authors.affiliation: School of Pharmaceutical Engineering and Life Science, Changzhou University , No. 1 Middle Gehu Road, Changzhou, Jiangsu Province 213164, China.
authors.forename: Hua-Dong
authors.initials: HD
authors.lastname: Xu
authors.forename: Zhi-Hong
authors.initials: ZH
authors.lastname: Jia
authors.forename: Ke
authors.initials: K
authors.lastname: Xu
authors.forename: Hao
authors.initials: H
authors.lastname: Zhou
authors.forename: Mei-Hua
authors.initials: MH
authors.lastname: Shen
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry; D028561:Transition Elements; D014230:Triazoles / Q000737:chemistry*
chemical_list: D058116:Lewis Acids; D008698:Mesylates; D009942:Organometallic Compounds; D013449:Sulfonamides; D028561:Transition Elements; D014230:Triazoles; C030011:carbene; D012238:Rhodium; C012077:trifluoromethanesulfonic acid; C062962:dirhodium tetraacetate; D008697:Methane