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Kinetic Resolution of 2-Substituted 1,2-Dihydroquinolines via Asymmetric Cu-Catalyzed Borylation Reaction

Abstract

A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation has been first realized. Under mild conditions, a variety of chiral 3-boryl-1,2,3,4-tetrahydroquinolines bearing two vicinal stereogenic centers and recovered 2-substituted 1,2-dihydroquinolines were simultaneously provided in 30 minutes in high yields with up to 99% ee (dr > 99:1) and almost uniform over 99% ee values, respectively, corresponding to kinetic selectivity factors of up to 569. Moreover, this protocol was successfully applied in the asymmetric synthesis of a selective estrogen receptor modulator.

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Publication details

The article was accepted on 11 Apr 2017 and first published on 19 Apr 2017


Article type: Edge Article
DOI: 10.1039/C7SC01556A
Citation: Chem. Sci., 2017, Accepted Manuscript
  • Open access: Creative Commons BY license
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    Kinetic Resolution of 2-Substituted 1,2-Dihydroquinolines via Asymmetric Cu-Catalyzed Borylation Reaction

    D. Kong, S. Han, R. Wang, M. Li, G. Zi and G. Hou, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC01556A

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