Abstract:
A primary amine-based aqueous ionic liquid-supported recyclable catalytic system for asymmetric Michael addition of aldehydes to maleimides has been developed. The best enantioselectivity (up to 84% ee) was attained at the [bmim]BF4/water 2 : 1 (v/v) ratio.
Citation:
S. V. Kochetkov, A. S. Kucherenko, S. G. Zlotin, “Asymmetric Michael addition of aldehydes to maleimides in primary amine-based aqueous ionic liquid-supported recyclable catalytic system”, Mendeleev Commun., 27:5 (2017), 473–475
Linking options:
https://www.mathnet.ru/eng/mendc2031
https://www.mathnet.ru/eng/mendc/v27/i5/p473
This publication is cited in the following 14 articles:
Barnali Jana, Monotosh Mondal, Shibashis Halder, Atanu Mahata, Sameer Saurav, Sushovan Paladhi, “Recent Advancement on the Organocatalyzed Asymmetric Conjugate Addition using Maleimide as a Potential Substrate”, Asian J Org Chem, 12:10 (2023)
Carles Rodríguez‐Escrich, Miquel A. Pericàs, Asymmetric Organocatalysis, 2023, 349
Viktória Kozma, György Szőllősi, “Enantioselective Michael addition of aldehydes to maleimides catalysed by surface-adsorbed natural amino acids”, Catal. Sci. Technol., 12:15 (2022), 4709
Alejandro Torregrosa-Chinillach, Rafael Chinchilla, “Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide”, Molecules, 27:19 (2022), 6668
José M. Landeros, Carlos Cruz‐Hernández, Eusebio Juaristi, “α‐Amino Acids and α,β‐Dipeptides Intercalated into Hydrotalcite: Efficient Catalysts in the Asymmetric Michael Addition Reaction of Aldehydes to N‐Substituted Maleimides”, Eur J Org Chem, 2021:37 (2021), 5117
Viktória Kozma, Ferenc Fülöp, György Szőllősi, “1,2‐Diamine‐Derived (thio)Phosphoramide Organocatalysts in Asymmetric Michael Additions”, Adv Synth Catal, 362:12 (2020), 2444
Xavier Marset, Diego J. Ramón, Gabriela Guillena, Catalyst Immobilization, 2020, 187
Zhi-Hong Du, Wen-Juan Qin, Bao-Xiu Tao, Meng Yuan, Chao-Shan Da, “N-Primary-amine tetrapeptide-catalyzed highly asymmetric Michael addition of aliphatic aldehydes to maleimides”, Org. Biomol. Chem., 18:35 (2020), 6899
K. A. Bykova, A. A. Kostenko, A. S. Kucherenko, S. G. Zlotin, “Asymmetric Michael reaction between aldehydes and nitroalkanes promoted by pyrrolidine-containing C2-symmetric organocatalysts”, Russ Chem Bull, 68:7 (2019), 1402
V. K. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, I. D. Firsin, A. A. Shiryaev, K. N. Gavrilov, A. V. Maximychev, A. M. Perepukhov, N. S. Goulioukina, I. P. Beletskaya, “Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis”, Mendeleev Commun., 29:1 (2019), 35–37
Alejandro Torregrosa-Chinillach, Adrien Moragues, Haritz Pérez-Furundarena, Rafael Chinchilla, Enrique Gómez-Bengoa, Gabriela Guillena, “Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide”, Molecules, 23:12 (2018), 3299
N. Z. Kiss, Z. Radai, I. Tihanyi, T. Szabó, G. T. Keglevich, “Microwave-assisted direct esterification of a cyclic phosphinic acid with phenols”, Mendeleev Commun., 28:1 (2018), 31–32
M. Yu. Ivanov, M. V. Fedin, “Nanoscale heterogeneities in ionic liquids: insights from EPR of spin probes”, Mendeleev Commun., 28:6 (2018), 565–573
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