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Updated: Jan 28, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
Alexander S Kucherenko1, Alexey A Kostenko1, Andrey N Komogortsev1
1N.D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky Prospect , Moscow 119991 , Russian Federation.
Abstract:
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.
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