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

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

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2018, Volume: 16, Number: 48, Pages: 9314-9318 Pages count : 5 DOI: 10.1039/c8ob02523a

Authors

Kostenko Alexey A ¹ , Kucherenko Alexander S ¹ , Komogortsev Andrey N ¹ , Lichitsky Boris V ¹ , Zlotin Sergei G ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, Russian Federation

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.

Kostenko A.A. , Kucherenko A.S. , Komogortsev A.N. , Lichitsky B.V. , Zlotin S.G.
Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by C2-symmetric organocatalysts
Organic & Biomolecular Chemistry. 2018. V.16. N48. P.9314-9318. DOI: 10.1039/c8ob02523a WOS Scopus OpenAlex

Web of science:	WOS:000453230000024
Scopus:	2-s2.0-85058474155
OpenAlex:	W2900365757

DB	Citing
OpenAlex	13
Scopus	15
Web of science	14