C-2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions

A very simple and highly efficient C-2-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 beta-dicarbonyl compounds reacted with nitroolefins, affording the correspondin...

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Published inJournal of organic chemistry Vol. 84; no. 7; pp. 4304 - 4311
Main Authors Kucherenko, Alexander S., Kostenko, Alexey A., Komogortsev, Andrey N., Lichitsky, Boris V., Fedotov, Michael Yu, Zlotin, Sergei G.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.04.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BETA-NITROOLEFINS
BOND DONORS
THIOUREA
1,3-DICARBONYL COMPOUNDS
NONCOVALENT
ALPHA,BETA-UNSATURATED IMIDES
KOJIC ACID-DERIVATIVES
CATALYSTS
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Summary:A very simple and highly efficient C-2-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 beta-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00252