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Issue 45, 2017
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Construction of tetrahydropyranoquinoline derivatives via an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction

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Abstract

Chiral functionalized tetrahydroquinolines and pyranoquinolines with multiple stereogenic centres have emerged as attractive structures for derivatizing bioactive complex molecules. Herein, we develop a novel, facile organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (E)-ethyl 4-(2-(4-methylphenylsulfon amido)phenyl)-2-oxobut-3-enoate and enals. This method enables a convenient, powerful, and atom-economical access to various desired tetrahydropyranoquinoline derivatives with control of four stereogenic centres in good yields (up to 88%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr and >99% ee, respectively).

Graphical abstract: Construction of tetrahydropyranoquinoline derivatives via an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction

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Publication details

The article was received on 05 Sep 2017, accepted on 12 Oct 2017 and first published on 12 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02231J
Citation: Org. Biomol. Chem., 2017,15, 9630-9637
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    Construction of tetrahydropyranoquinoline derivatives via an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction

    L. Dai, Y. Hou, L. Zhang, Z. Chen, X. Zeng and G. Zhong, Org. Biomol. Chem., 2017, 15, 9630
    DOI: 10.1039/C7OB02231J

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