Green asymmetric synthesis of tetrahydroquinolines in carbon dioxide medium promoted by lipophilic bifunctional tertiary amine – squaramide organocatalysts

Green asymmetric synthesis of tetrahydroquinolines in carbon dioxide medium promoted by lipophilic bifunctional tertiary amine – squaramide organocatalysts Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2018, Volume: 74, Number: 1, Pages: 157-164 Pages count : 8 DOI: 10.1016/j.tet.2017.11.057

Authors

Filatova Evgeniya V. ¹ , Turova Olga V. ¹ , Nigmatov Albert G. ¹ , Zlotin Sergei G. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russia

Novel pseudo-enantiomeric bifunctional tertiary amine-squaramides modified with long-chained alkoxy or polyfluoroalkoxy groups, have been synthesized. They catalyzed the asymmetric double-Michael cascade reactions of o-N-tosylaminophenyl α,β-unsaturated ketones with α-nitroolefins in carbon dioxide medium at significantly lower pressure (75 bar) and temperature (35 °C), than known less lipophilic catalysts. Both enantiomers of the pharmacologically valuable methoxy-substituted tetrahydroquinoline derivatives can be prepared in moderate to high yield with promising enantioselectivity (up to 98% ee) under the optimized conditions.

Filatova E.V. , Turova O.V. , Nigmatov A.G. , Zlotin S.G.
Green asymmetric synthesis of tetrahydroquinolines in carbon dioxide medium promoted by lipophilic bifunctional tertiary amine – squaramide organocatalysts
Tetrahedron. 2018. V.74. N1. P.157-164. DOI: 10.1016/j.tet.2017.11.057 WOS Scopus OpenAlex

Web of science:	WOS:000418728200021
Scopus:	2-s2.0-85036641050
OpenAlex:	W2769688439

DB	Citing
OpenAlex	18
Scopus	17
Web of science	15