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Issue 6, 2017
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Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

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Abstract

A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation has been realized for the first time. Under mild conditions, a variety of chiral 3-boryl-1,2,3,4-tetrahydroquinolines containing two vicinal stereogenic centers as well as the recovered 2-substituted 1,2-dihydroquinolines were afforded after 30 minutes in high yields with up to 99% ee (dr > 99 : 1) and over 98% ee values, respectively, corresponding to kinetic selectivity factors of up to 569. Moreover, this protocol was successfully applied to the asymmetric synthesis of a selective estrogen receptor modulator.

Graphical abstract: Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

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Publication details

The article was received on 18 Feb 2017, accepted on 11 Apr 2017 and first published on 19 Apr 2017


Article type: Edge Article
DOI: 10.1039/C7SC01556A
Citation: Chem. Sci., 2017,8, 4558-4564
  • Open access: Creative Commons BY license
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    Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

    D. Kong, S. Han, R. Wang, M. Li, G. Zi and G. Hou, Chem. Sci., 2017, 8, 4558
    DOI: 10.1039/C7SC01556A

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