Аннотация:
Novel (4R)-HO-(2S)-Pro-(S)-Val derivative tagged to 1-methylimidazolium cation and PF−6 anion efficiently catalyzes asymmetric aldol reactions of cyclic ketones with aromatic aldehydes in aqueous environment to afford the corresponding aldols in high yield with moderate to high anti-diastereo- (dr up to 99:1) and enantioselectivity (up to 98% ee). The catalyst was recycled 9 times in the same reaction without any decrease in selectivity values.
Образец цитирования:
A. S. Kucherenko, V. V. Perepelkin, G. M. Zhdankina, G. V. Kryshtal, E. Srinivasan, H. Inani, S. G. Zlotin, “Ionic liquid supported 4-HO-Pro-Val derived organocatalysts for asymmetric aldol reactions in the presence of water”, Mendeleev Commun., 26:5 (2016), 388–390
\RBibitem{KucPerZhd16}
\by A.~S.~Kucherenko, V.~V.~Perepelkin, G.~M.~Zhdankina, G.~V.~Kryshtal, E.~Srinivasan, H.~Inani, S.~G.~Zlotin
\paper Ionic liquid supported 4-HO-Pro-Val derived organocatalysts for asymmetric aldol reactions in the presence of water
\jour Mendeleev Commun.
\yr 2016
\vol 26
\issue 5
\pages 388--390
\mathnet{http://mi.mathnet.ru/mendc2222}
\crossref{https://doi.org/10.1016/j.mencom.2016.09.007}
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc2222
https://www.mathnet.ru/rus/mendc/v26/i5/p388
Эта публикация цитируется в следующих 17 статьяx:
Carles Rodríguez‐Escrich, Miquel A. Pericàs, Asymmetric Organocatalysis, 2023, 349
Karolina Zalewska, Małgorzata E. Zakrzewska, Luis C. Branco, “Chiral Ionic Liquids Based on l-Cysteine Derivatives for Asymmetric Aldol Reaction”, Catalysts, 12:1 (2022), 47
Raúl Porcar, Eduardo García-Verdugo, Belén Altava, Maria Isabel Burguete, Santiago V. Luis, “Chiral Imidazolium Prolinate Salts as Efficient Synzymatic Organocatalysts for the Asymmetric Aldol Reaction”, Molecules, 26:14 (2021), 4190
Eusebio Juaristi, “Recent developments in next generation (S)-proline-derived chiral organocatalysts”, Tetrahedron, 88 (2021), 132143
Durgesh Gurukkala Valapil, Manasa Kadagathur, Nagula Shankaraiah, “Stereoselective Aldol and Conjugate Addition Reactions Mediated by Proline‐Based Catalysts and Its Analogues: A Concise Review”, Eur J Org Chem, 2021:37 (2021), 5288
Snehkrishn A. Chaubey, Niranjan Patra, Roli Mishra, “Synthesis of novel proline-based imidazolium ionic liquids”, Monatsh Chem, 151:9 (2020), 1409
Kazumasa Kon, Yoshihito Kohari, Miki Murata, “Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins”, Tetrahedron Letters, 60:5 (2019), 415
Sudipto Bhowmick, Li Zhang, Guanghui Ouyang, Minghua Liu, “Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction”, ACS Omega, 3:7 (2018), 8329
Chao-Xian Yan, Pan-Pan Zhou, Fang-Ling Yang, Rui-Zhi Wu, Xing Yang, Fan Yang, Xiangfeng Shao, “Chiral bisoxazoline catalyzed decarboxylative aldol reactions between β-carbonyl acids and trifluoroacetaldehyde hemiacetals as well as trifluoroacetaldehyde: the mechanism, the origin of enantioselectivity and the role of a catalyst”, Org. Chem. Front., 5:18 (2018), 2692
Babak Karimi, Mina Tavakolian, Maryam Akbari, Fariborz Mansouri, “Ionic Liquids in Asymmetric Synthesis: An Overall View from Reaction Media to Supported Ionic Liquid Catalysis”, ChemCatChem, 10:15 (2018), 3173
M. Yu. Ivanov, M. V. Fedin, “Nanoscale heterogeneities in ionic liquids: insights from EPR of spin probes”, Mendeleev Commun., 28:6 (2018), 565–573
O. V. Fedorova, Yu. A. Titova, I. G. Ovchinnikova, G. L. Rusinov, V. N. Charushin, “4-Hydroxyproline containing podands as new chiralcatalysts for the asymmetric Biginelli reaction”, Mendeleev Commun., 28:4 (2018), 357–358
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
Arturo Obregón-Zúñiga, Eusebio Juaristi, “(2S,4R)-Hyp-(S)-Phe-OMe dipeptide supported on imidazolium tagged molecules as recoverable organocatalysts for asymmetric aldol reactions using water as reaction medium”, Tetrahedron, 73:36 (2017), 5373
Majid M. Heravi, Vahideh Zadsirjan, Mahzad Dehghani, Nastaran Hosseintash, “Current applications of organocatalysts in asymmetric aldol reactions: An update”, Tetrahedron: Asymmetry, 28:5 (2017), 587
A. V. Okhlobystina, A. O. Okhlobystin, N. N. Letichevskaya, V. F. Abdulaeva, N. O. Movchan, N. T. Berberova, “An alternative method for the desulfurization of hydrocarbon fuels”, Mendeleev Commun., 27:1 (2017), 104–105
M. G. Chernysheva, A. E. Averina, O. A. Soboleva, G. A. Badun, “Radionuclide and tensiometry approaches to studying lysozyme behaviors in water–ionic liquid systems”, Mendeleev Commun., 27:3 (2017), 296–298
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