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Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by C2-symmetric organocatalysts

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Abstract

An efficient sterically hindered C2-symmetric bifunctional tertiary amine–squaramide organocatalyst for the asymmetric Michael addition/hemiketalization domino reaction of kojic acid derivatives with β,γ-unsaturated α-ketoesters has been designed. Pharmacology-relevant functionalized 2,3,4,8-tetrahydropyrano[3,2-b]pyran derivatives were produced over the catalyst in as low as 1 mol% with up to 99% yield and 99% ee. The procedure is at least 30-fold scalable and the catalyst is readily reusable in the catalytic reaction via acid–base extraction. Acylation of the products with (S)- or rac-ibuprofen and with undec-10-enoic acid afforded the corresponding chiral esters containing two privileged pharmacophoric motifs.

Graphical abstract: Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by C2-symmetric organocatalysts

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Publication details

The article was received on 11 Oct 2018, accepted on 04 Nov 2018 and first published on 06 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02523A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by C2-symmetric organocatalysts

    A. A. Kostenko, A. S. Kucherenko, A. N. Komogortsev, B. V. Lichitsky and S. G. Zlotin, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02523A

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