title: Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts.
abstract: A highly enantioselective rhodium(I)-catalyzed dearomative arylation or alkenylation of easily available N-alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99 % ee. This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (-)-angustureine and (+)-cuspareine.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China.
authors.forename: Yunlong
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China.
authors.forename: Dongdong
authors.initials: D
authors.lastname: Zhang
authors.affiliation: School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P.R. China. haowei@sjtu.edu.cn.
authors.forename: Hao
authors.initials: H
authors.lastname: Wei
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, P.R. China.
authors.forename: Min
authors.initials: M
authors.lastname: Shi
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P.R. China. feijunwang@ecust.edu.cn.
authors.forename: Feijun
authors.initials: F
authors.lastname: Wang
keywords: boron; heterocycles; nucleophilic addition; rhodium; total synthesis