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

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

Journal

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

Output data

Year: 2018, Volume: 16, Number: 35, Pages: 6423-6429 Pages count : 7 DOI: 10.1039/c8ob01576g

Authors

Kochetkov Sergei Viktorovich ¹ , Kucherenko Alexander ¹ , Zlotin Sergei Grigorievich ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia

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.

Kochetkov S.V. , Kucherenko A. , Zlotin S.G.
Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines
Organic & Biomolecular Chemistry. 2018. V.16. N35. P.6423-6429. DOI: 10.1039/c8ob01576g WOS Scopus OpenAlex

Web of science:	WOS:000444484800007
Scopus:	2-s2.0-85053526611
OpenAlex:	W2883059706

DB	Citing
OpenAlex	16
Scopus	16
Web of science	17