Tertiary Amine-Derived Ionic Liquid-Supported Squaramide as a Recyclable Organocatalyst for Noncovalent “On Water” Catalysis

Tertiary Amine-Derived Ionic Liquid-Supported Squaramide as a Recyclable Organocatalyst for Noncovalent “On Water” Catalysis Full article

Journal

ACS Catalysis
ISSN: 2155-5435

Output data

Year: 2017, Volume: 7, Number: 4, Pages: 2981-2989 Pages count : 9 DOI: 10.1021/acscatal.7b00562

Authors

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

Affiliations

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

Chiral tertiary amine-derived ionic liquid-supported squaramide was synthesized from available precursors and applied as an efficient organocatalyst for asymmetric Michael additions of β-dicarbonyl compounds to α-nitroolefins in the presence of water. Corresponding Michael adducts were generated under proposed conditions in nearly quantitative yield with high enantioselectivity (up to 99% ee). Useful precursors to pharmaceutically important chiral β-amino acids and anticonvulsant Pregabalin were conveniently prepared using the developed “on water” protocol. The catalyst is readily recoverable and reusable over 30 times without a significant decrease of catalytic reaction activity and selectivity.

Tukhvatshin R.S. , Kucherenko A.S. , Nelyubina Y.V. , Zlotin S.G.
Tertiary Amine-Derived Ionic Liquid-Supported Squaramide as a Recyclable Organocatalyst for Noncovalent “On Water” Catalysis
ACS Catalysis. 2017. V.7. N4. P.2981-2989. DOI: 10.1021/acscatal.7b00562 WOS Scopus OpenAlex

Web of science:	WOS:000398986700085
Scopus:	2-s2.0-85019688200
OpenAlex:	W2597122855

DB	Citing
OpenAlex	63
Scopus	69
Web of science	60