title: Enantioselective Synthesis of 3a-Amino-Pyrroloindolines by Copper-Catalyzed Direct Asymmetric Dearomative Amination of Tryptamines.
abstract: A direct asymmetric dearomative amination of tryptamines with O-(2,4-dinitrophenyl)hydroxylamine (DPH) was achieved using CuBr-bisoxazoline complex as a catalyst, affording 3a-amino-pyrroloindolines in good to excellent enantioselectivity under mild reaction conditions. Furthermore, the synthetic value of this method was demonstrated in the total synthesis of (-)-psychotriasine in a highly concise manner.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (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 (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 (China).
authors.forename: Zhong-Bo
authors.initials: ZB
authors.lastname: Zheng
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China). tangy@sioc.ac.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China). tangy@sioc.ac.cn.
authors.forename: Yong
authors.initials: Y
authors.lastname: Tang
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (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 (China). slyou@sioc.ac.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China). slyou@sioc.ac.cn.
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D007211:Indoles; D014363:Tryptamines; C030820:tryptamine; D003300:Copper
keywords: asymmetric catalysis; copper; dearomatization; pyrroloindolines; tryptamines