title: The cyano group as a traceless activation group for the intermolecular [3+2] cycloaddition of azomethine ylides: a five-step synthesis of (±)-isoretronecanol.
abstract: The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted pyrrolidines. The transformation includes the silver acetate catalyzed intermolecular 1,3-dipolar cycloaddition of α-iminonitriles and an unprecedented sodium borohydride induced reductive decyanation reaction. A diverse array of substrates is amenable to this transformation. The methodology was further extended to a five-step total synthesis of the pyrrolizidine natural product isoretronecanol.
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China).
authors.forename: Jundong
authors.initials: J
authors.lastname: Li
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China).
authors.forename: Huaibo
authors.initials: H
authors.lastname: Zhao
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China).
authors.forename: Xunjin
authors.initials: X
authors.lastname: Jiang
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China).
authors.forename: Xiance
authors.initials: X
authors.lastname: Wang
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China).
authors.forename: Haiming
authors.initials: H
authors.lastname: Hu
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China).
authors.forename: Lei
authors.initials: L
authors.lastname: Yu
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China). ydzhang@xmu.edu.cn.
authors.forename: Yandong
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D001688:Biological Products; D011763:Pyrrolizidine Alkaloids; D013882:Thiosemicarbazones; C512188:azomethine; C051740:isoretronecanol
keywords: cycloaddition; pyrrolidines; reductive decyanation; total synthesis; traceless activation