title: Catalytic asymmetric 1,3-dipolar [3 + 6] cycloaddition of azomethine ylides with 2-acyl cycloheptatrienes: efficient construction of bridged heterocycles bearing piperidine moiety.
abstract: Conjugated cyclic trienes without nonbenzenoid aromatic characteristic were successfully employed as fine-tunable dipolarophiles in the Cu(I)-catalyzed asymmetric azomethine ylide-involved 1,3-dipolar [3 + 6] cycloaddition for the first time, affording a variety of bridged heterocycles bearing piperidine moiety in good yield with exclusive regioselectivity and excellent stereoselectivity. 2-Acyl group is the key factor that determines the annulation preferentially through [3 + 6]-pathway, while 2-ester group modulates the annulation through [3 + 2]-pathway.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University , Wuhan, China 430072.
authors.forename: Qing-Hua
authors.initials: QH
authors.lastname: Li
authors.forename: Liang
authors.initials: L
authors.lastname: Wei
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D003508:Cycloheptanes; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D010880:Piperidines; D013882:Thiosemicarbazones; C512188:azomethine; C032727:piperidine