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Issue 35, 2018
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Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines

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Abstract

Novel C2-symmetric N,N′-bis(2-amino-1,2-diphenylethyl)squaramides with 1,2-di(pyridin-2-yl)ethane and 1,2-diphenylethane spacer groups were designed and applied as organocatalysts in asymmetric additions of 4-hydroxycoumarin and 4-hydroxy-6-methyl-2H-pyran-2-one to α,β-unsaturated ketones. Both enantiomers of the anticoagulant warfarin and its analogs were prepared in up to 96% yield and with 96% ee. Recyclability of the developed catalysts and synthetic utility of the prepared Michael adducts for asymmetric synthesis of potential chiral medications via acylation reactions were demonstrated.

Graphical abstract: Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines

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Publication details

The article was received on 04 Jul 2018, accepted on 24 Jul 2018 and first published on 24 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01576G
Citation: Org. Biomol. Chem., 2018,16, 6423-6429

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    Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines

    S. V. Kochetkov, A. S. Kucherenko and S. G. Zlotin, Org. Biomol. Chem., 2018, 16, 6423
    DOI: 10.1039/C8OB01576G

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