C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions

C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 7, Pages: 4304-4311 Pages count : 8 DOI: 10.1021/acs.joc.9b00252

Authors

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

Affiliations

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

A very simple and highly efficient C2-symmetric tertiary amine-squaramide organocatalyst for asymmetric Michael reactions has been elaborated. In the presence of only 1 mol % of this catalyst, kojic acid derivatives and β-dicarbonyl compounds reacted with nitroolefins, affording the corresponding adducts in a nearly quantitative yield with an enantioselectivity up to 99% ee. The kojic acid-derived adducts could be efficiently produced under “green” conditions (in 96% EtOH or pure water). Moreover, due to the very low solubility in organic solvents, the developed nonsupported catalyst could be readily recovered and reused in catalytic reactions up to 7 times. Utmost availability (one-step synthesis without chromatographic purification), high level of stereoinduction, low efficient loading, and recyclability make it attractive for industrial application in the pharmaceutical industry.

Kucherenko A.S. , Kostenko A.A. , Komogortsev A.N. , Lichitsky B.V. , Fedotov M.Y. , Zlotin S.G.
C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
Journal of Organic Chemistry. 2019. V.84. N7. P.4304-4311. DOI: 10.1021/acs.joc.9b00252 WOS Scopus OpenAlex

Web of science:	WOS:000464250800053
Scopus:	2-s2.0-85063127206
OpenAlex:	W2920792191

DB	Citing
OpenAlex	35
Web of science	33
Scopus	35