Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine

Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2018, Volume: 2018, Number: 48, Pages: 7000-7008 Pages count : 9 DOI: 10.1002/ejoc.201801423

Authors

Tukhvatshin Rinat S. ¹ , Kucherenko Alexander S. ¹ , Nelyubina Yulia V. ² , Zlotin Sergei G. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28, Vavilova str, 119991 Moscow, Russia

The most recyclable ionic liquid-supported bifunctional tertiary amine–squaramide organocatalyst for the asymmetric domino reaction has been found. Over this catalyst, ortho-aminochalcones protected with Tosyl or Nosyl groups underwent the aza-Michael/Michael domino reaction with nitroolefins to afford corresponding 2,3,4-trisubstituted tetrahydroquinolines as single diastereomers in nearly quantitative yield with up to 99 % ee. The catalyst was readily separated from the reaction mixture via a simple centrifugation/decantation workup and 19 times reused in the catalytic reaction without noticeable conversion or enantioselectivity reduction. The N-nosylated products proved their synthetic value for pharmacology given their facile conversion to fused pirrolidino-tetrahydroquinolines of high diastreomeric and enantiomeric purity via successive deprotection and reductive amination.

Tukhvatshin R.S. , Kucherenko A.S. , Nelyubina Y.V. , Zlotin S.G.
Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic‐Liquid‐Supported Bifunctional Tertiary Amine
European Journal of Organic Chemistry. 2018. V.2018. N48. P.7000-7008. DOI: 10.1002/ejoc.201801423 WOS Scopus OpenAlex

Web of science:	WOS:000454532300021
Scopus:	2-s2.0-85057470305
OpenAlex:	W2898790346

DB	Citing
OpenAlex	14
Scopus	17
Web of science	11