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Issue 48, 2018
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Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines via a squaramide-catalyzed cascade reaction

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Abstract

A bifunctional squaramide-catalyzed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral spirothiazolidinone tetrahydroquinolines with three contiguous stereocenters has been developed. This cascade reaction proceeded well under mild conditions, and afforded the desired products in high to excellent yields (up to >99% yield) with excellent diastereoselectivities (>25 : 1 dr) and high enantioselectivities (up to 96% ee). More importantly, both the amplification and the derivation experiments do not affect the stereoselectivity.

Graphical abstract: Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines via a squaramide-catalyzed cascade reaction

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Publication details

The article was received on 03 Nov 2018, accepted on 22 Nov 2018 and first published on 23 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02731E
Citation: Org. Biomol. Chem., 2018,16, 9390-9401
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    Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines via a squaramide-catalyzed cascade reaction

    Y. Song and D. Du, Org. Biomol. Chem., 2018, 16, 9390
    DOI: 10.1039/C8OB02731E

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