title: Copper(I)-Catalyzed Asymmetric Dearomatization of Indole Acetamides with 3-Indolylphenyliodonium Salts.
abstract: The rapid and direct asymmetric synthesis of 3-(3a-indolyl)hexahydropyrroloindoline motifs is an extremely important part of the total synthesis of several alkaloid structures. Herein, an intermolecular, asymmetric cascade dearomatization reaction of indole acetamides with 3-indolylphenyliodonium salts has been developed. This protocol provides a straightforward access to 3-(3a-indolyl)hexahydropyrroloindolines bearing an all-carbon quaternary stereocenter at the C3 position of the indoline ring with high enantioselectivities. The utility of the protocol has been demonstrated by the formal asymmetric synthesis of folicanthine.
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.
authors.forename: Chuan
authors.initials: C
authors.lastname: Liu
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.
authors.forename: Ji-Cheng
authors.initials: JC
authors.lastname: Yi
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.
authors.forename: Xiao-Wei
authors.initials: XW
authors.lastname: Liang
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.
authors.forename: Ren-Qi
authors.initials: RQ
authors.lastname: Xu
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.
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Dai
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. slyou@sioc.ac.cn.|Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin, 300072, P. R. China. slyou@sioc.ac.cn.
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D007211:Indoles; D003300:Copper
keywords: asymmetric catalysis; dearomatization; indole; iodonium salts; natural products