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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Polyacrylic Acid Supported L-proline as an Effective Heterogeneous Catalyst for the Direct Asymmetric Aldol Reaction

Author(s): Cuizhi Zhang, Yanchao Fan, Sijia Wang, Shaojie Liu*, Xiaomeng Chu* and Erjun Tang*

Volume 21, Issue 1, 2024

Published on: 24 May, 2023

Page: [47 - 60] Pages: 14

DOI: 10.2174/1570179420666230330085329

Price: $65

Abstract

Introduction: L-proline is an efficient chiral small-molecule organocatalyst for the direct asymmetric aldol reaction between unmodified acetone and a variety of aldehydes.

Methods: However, it is difficult to separate from the reaction medium for reuse. In this work, polyacrylic acid (PAA) supported The acylation reaction between L-hydroxyproline and PAA prepared lproline (P(AA-co-PA)) catalysts with various catalyst loadings. Fourier characterized them transforms infrared spectroscopy, nuclear magnetic resonance spectrum, gel permeation chromatography and thermogravimetry analysis.

Results: These macromolecular catalysts were used to catalyze acetone and benzaldehydes' direct asymmetric aldol reaction. The influence of the catalyst structure on the catalytic performance was studied, and the reaction conditions were optimized.

Conclusion: The results showed that P(AA-co-PA) with 50 mol% catalyst loading had excellent catalytic performance, much higher than that of L-proline and L-hydroxyproline. Its recovery was achieved by simple filtration. After being reused 7 times, its catalytic performance was still higher than that of L-proline.

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[1]
Liu, H.; Peng, L.; Zhang, T.; Li, Y. l-Proline catalyzed asymmetric aldol reactions of protected hydroxyacetone. New J. Chem., 2003, 27(8), 1159-1160.
[http://dx.doi.org/10.1039/b304019b]
[2]
Hubin, P.O.; Jacquemin, D.; Leherte, L.; Vercauteren, D.P. Parameterization of the ReaxFF reactive force field for a proline-catalyzed aldol reaction. J. Comput. Chem., 2016, 37(29), 2564-2572.
[http://dx.doi.org/10.1002/jcc.24481] [PMID: 27592688]
[3]
Xu, L.; Wang, F.; Huang, J.; Yang, C.; Yu, L.; Fan, Y. l -Proline and thiourea co-catalyzed condensation of acetone. Tetrahedron, 2016, 72(27-28), 4076-4080.
[http://dx.doi.org/10.1016/j.tet.2016.05.039]
[4]
Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C.F., III Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions. J. Am. Chem. Soc., 2001, 123(22), 5260-5267.
[http://dx.doi.org/10.1021/ja010037z] [PMID: 11457388]
[5]
List, B.; Martínez, A.; Zumbansen, K.; Döhring, A.; van Gemmeren, M. Improved conditions for the proline-catalyzed aldol reaction of acetone with aliphatic aldehydes. Synlett, 2014, 25(7), 932-934.
[http://dx.doi.org/10.1055/s-0033-1340919]
[6]
Krištofíková, D.; Modrocká, V. Mečiarová, M.; Šebesta, R. Green asymmetric organocatalysis. ChemSusChem, 2020, 13(11), 2828-2858.
[http://dx.doi.org/10.1002/cssc.202000137] [PMID: 32141177]
[7]
Al-Momani, L.; Lataifeh, A. Asymmetric aldol “Reaction in water” using ferrocene-amino acid conjugates. Ind. Eng. Chem. Res., 2022, 61(6), 2417-2424.
[http://dx.doi.org/10.1021/acs.iecr.1c04725]
[8]
Xiang, S.H.; Tan, B. Advances in asymmetric organocatalysis over the last 10 years. Nat. Commun., 2020, 11(1), 3786.
[http://dx.doi.org/10.1038/s41467-020-17580-z] [PMID: 32728115]
[9]
Mandalapu, D. L-proline and d-proline (chiral amino acid catalysts). Synlett, 2015, 26(5), 707-708.
[http://dx.doi.org/10.1055/s-0034-1380270]
[10]
Dalko, P.I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem. Int. Ed., 2004, 43(39), 5138-5175.
[http://dx.doi.org/10.1002/anie.200400650] [PMID: 15455437]
[11]
Cukrowski, I.; Dhimba, G.; Riley, D.L. A reaction energy profile and fragment attributed molecular system energy change (FAMSEC)-based protocol designed to uncover reaction mechanisms: a case study of the proline-catalysed aldol reaction. Phys. Chem. Chem. Phys., 2019, 21(30), 16694-16705.
[http://dx.doi.org/10.1039/C9CP03046H] [PMID: 31321390]
[12]
Tafida, U.I.; Uzairu, A.; Abechi, S.E. Mechanism and rate constant of proline-catalysed asymmetric aldol reaction of acetone and p-nitrobenzaldehyde in solution medium: Density-functional theory computation. J. Adv. Res., 2018, 12, 11-19.
[http://dx.doi.org/10.1016/j.jare.2018.03.002] [PMID: 30013799]
[13]
Bhati, M.; Kumari, K.; Easwar, S. Probing the synergistic catalytic model: a rationally designed urea-tagged proline catalyst for the direct asymmetric aldol reaction. J. Org. Chem., 2018, 83(15), 8225-8232.
[http://dx.doi.org/10.1021/acs.joc.8b00962] [PMID: 29847121]
[14]
Panday, S.K. Advances in the chemistry of proline and its derivatives: an excellent amino acid with versatile applications in asymmetric synthesis. Tetrahedron Asymmetry, 2011, 22(20-22), 1817-1847.
[http://dx.doi.org/10.1016/j.tetasy.2011.09.013]
[15]
Calderón, F.; Doyagüez, E.G.; Cheong, P.H.Y.; Fernández-Mayoralas, A.; Houk, K.N. Origins of the double asymmetric induction on proline-catalyzed aldol reactions. J. Org. Chem., 2008, 73(20), 7916-7920.
[http://dx.doi.org/10.1021/jo800934b] [PMID: 18811197]
[16]
Giacalone, F.; Gruttadauria, M.; Agrigento, P.; Lo Meo, P.; Noto, R. Advances towards highly active and stereoselective simple and cheap proline-based organocatalysts. Eur. J. Org. Chem., 2010, 2010(29), 5696-5704.
[http://dx.doi.org/10.1002/ejoc.201000913]
[17]
Bhowmick, S.; Kunte, S.S.; Bhowmick, K.C. The smallest organocatalyst in highly enantioselective direct aldol reaction in wet solvent-free conditions. RSC Advances, 2014, 4(46), 24311-24315.
[http://dx.doi.org/10.1039/C4RA02690J]
[18]
Northrup, A.B.; MacMillan, D.W.C. Two-step synthesis of carbohydrates by selective aldol reactions. Science, 2004, 305(5691), 1752-1755.
[http://dx.doi.org/10.1126/science.1101710] [PMID: 15308765]
[19]
Martínez-Castañeda, Á.; Rodríguez-Solla, H.; Concellón, C.; del Amo, V. Switching diastereoselectivity in proline-catalyzed aldol reactions. J. Org. Chem., 2012, 77(22), 10375-10381.
[http://dx.doi.org/10.1021/jo3020352] [PMID: 23101761]
[20]
Yu, L.J.; Blyth, M.T.; Coote, M.L. Re-examination of proline-catalyzed intermolecular aldol reactions: An ab initio kinetic modelling study. Top. Catal., 2022, 65(1-4), 354-365.
[http://dx.doi.org/10.1007/s11244-021-01501-5]
[21]
Marquez, C.; Metzger, J.O. ESI-MS study on the aldol reaction catalyzed by l-proline. Chem. Commun., 2006, 14(14), 1539-1541.
[http://dx.doi.org/10.1039/b518288c] [PMID: 16575453]
[22]
Hirose, M.; Fujiwara, S.; Ishigami, T.; Suga, K.; Okamoto, Y.; Umakoshi, H. Liposome membranes assist the L-proline-catalyzed aldol reaction of acetone and p-nitrobenzaldehyde in water. Chem. Lett., 2018, 47(7), 931-934.
[http://dx.doi.org/10.1246/cl.180180]
[23]
Zhang, L.; Ding, W.B.; Yu, Y.P.; Zou, H.B. Direct asymmetric aldol reaction using MBHA resin-supported peptide containing l-proline unit. Chin. Chem. Lett., 2009, 20(9), 1065-1067.
[http://dx.doi.org/10.1016/j.cclet.2009.04.034]
[24]
Chen, J.; Yu, H.; Tu, D.; Shen, L. l-Proline functionalized metal-organic framework PCN-261 as catalyst for aldol reaction. Inorg. Chem. Commun., 2019, 107, 107448.
[http://dx.doi.org/10.1016/j.inoche.2019.107448]
[25]
Zhao, Y.B.; Zhang, L.W.; Wu, L.Y.; Zhong, X.; Li, R.; Ma, J.T. Silica-supported pyrrolidine–triazole, an insoluble, recyclable organocatalyst for the enantioselective Michael addition of ketones to nitroalkenes. Tetrahedron Asymmetry, 2008, 19(11), 1352-1355.
[http://dx.doi.org/10.1016/j.tetasy.2008.05.011]
[26]
Szőri, K.; Réti, B.; Szőllősi, G.; Hernádi, K.; Bartók, M. Comparative study of graphite-oxide and graphene-oxide supported proline organocatalysts in asymmetric aldol addition. Top. Catal., 2016, 59(13-14), 1227-1236.
[http://dx.doi.org/10.1007/s11244-016-0643-6]
[27]
Chronopoulos, D.D.; Tsakos, M.; Karousis, N.; Kokotos, C.G.; Tagmatarchis, N. Fullerene–proline hybrids: Synthesis, characterization and organocatalytic properties in aldol reactions. Mater. Lett., 2014, 137, 343-346.
[http://dx.doi.org/10.1016/j.matlet.2014.09.031]
[28]
Benaglia, M.; Puglisi, A.; Cozzi, F. Polymer-supported organic catalysts. Chem. Rev., 2003, 103(9), 3401-3430.
[http://dx.doi.org/10.1021/cr010440o] [PMID: 12964876]
[29]
Kassem, T.; Jia, X.; Zhu, X.X.; Lubell, W.D. Poly (vinyl alcohol)-graft-poly (ethylene glycol)-supported hydroxyproline catalysis of stereoselective aldol reactions. Macromol. Symp., 2010, 297(1), 101-107.
[http://dx.doi.org/10.1002/masy.200900087]
[30]
Xu, M.L.; Huang, M.J.; Zhang, M.; Yu, L.; Fan, Y. Design and preparation of polymer resin-supported proline catalyst with industrial application potential. ChemistrySelect, 2016, 1(9), 1933-1937.
[http://dx.doi.org/10.1002/slct.201600404]
[31]
Li, C.; Wang, J.; Ding, H. Recyclable helical poly (phenyl isocyanide)-supported L-proline catalyst for direct asymmetric aldol reaction in brine. Catal. Lett., 2021, 151(4), 1180-1190.
[http://dx.doi.org/10.1007/s10562-020-03369-8]
[32]
Lu, A.; Smart, T.P.; Epps, T.H., III; Longbottom, D.A.; O’Reilly, R.K. L-proline functionalized polymers prepared by RAFT polymerization and their assemblies as supported organocatalysts. Macromolecules, 2011, 44(18), 7233-7241.
[http://dx.doi.org/10.1021/ma201256m] [PMID: 22053116]
[33]
Nazari, S.; Keshavarz, M. Amberlite-supported L-prolinate: A novel heterogeneous organocatalyst for the three-component synthesis of 4H-pyrano[2,3-c]pyrazole derivatives. Russ. J. Gen. Chem., 2017, 87(3), 539-545.
[http://dx.doi.org/10.1134/S1070363217030252]
[34]
Zou, J.; Zhao, W.; Li, R.; Zhang, H.; Cui, Y. Synthesis of PVC-TEPA-supported proline derivative and its catalytic behavior in the direct asymmetric aldol reaction. J. Appl. Polym. Sci., 2010, 118, 1020-1026. [https://doi.org/10.1002/app.29892
[35]
Li, X.; Wang, S.; Wang, K.; Jia, X.; Hu, Z. Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds. RSC Advances, 2018, 8(74), 42292-42299.
[http://dx.doi.org/10.1039/C8RA08712A] [PMID: 35558415]
[36]
Riente, P.; Mendoza, C.; Pericás, M.A. Functionalization of Fe3O4 magnetic nanoparticles for organocatalytic Michael reactions. J. Mater. Chem., 2011, 21(20), 7350-7355.
[http://dx.doi.org/10.1039/c1jm10535c]
[37]
Wang, B.G.; Ma, B.C.; Wang, Q.; Wang, W. Wang, Wei. Superparamagnetic nanoparticle-supported (s)-diphenyl-prolinol trimethylsilyl ether as a recyclable catalyst for asymmetric Michael addition in water. Adv. Synth. Catal., 2010, 352(17), 2923-2928.
[http://dx.doi.org/10.1002/adsc.201000508]
[38]
Yacob, Z.; Nan, A.; Liebscher, J. Proline-functionalized magnetic core-shell nanoparticles as efficient and recyclable organocatalysts for aldol reactions. Adv. Synth. Catal., 2012, 354(17), 3259-3264.
[http://dx.doi.org/10.1002/adsc.201200359]
[39]
Kong, Y.; Tan, R.; Zhao, L.; Yin, D.; Yin, D. l-Proline supported on ionic liquid-modified magnetic nanoparticles as a highly efficient and reusable organocatalyst for direct asymmetric aldol reaction in water. Green Chem., 2013, 15(9), 2422-2433.
[http://dx.doi.org/10.1039/c3gc40772a]
[40]
Sóti, P.L.; Yamashita, H.; Sato, K.; Narumi, T.; Toda, M.; Watanabe, N.; Marosi, G.; Mase, N. Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions. Tetrahedron, 2016, 72(16), 1984-1990.
[http://dx.doi.org/10.1016/j.tet.2016.02.065]
[41]
Bellis, E.; Kokotos, G. Proline-modified poly(propyleneimine) dendrimers as catalysts for asymmetric aldol reactions. J. Mol. Catal. Chem., 2005, 241(1-2), 166-174.
[http://dx.doi.org/10.1016/j.molcata.2005.05.047]
[42]
Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. Poly(ethylene glycol)-supported proline: a versatile catalyst for the enantioselective aldol and iminoaldol reactions. Adv. Synth. Catal., 2002, 344(5), 533-542.
[http://dx.doi.org/10.1002/1615-4169(200207)344:5<533:AID-ADSC533>3.0.CO;2-Y]
[43]
Llanes, P.; Sayalero, S.; Rodríguez-Escrich, C.; Pericàs, M.A. Asymmetric cross- and self-aldol reactions of aldehydes in water with a polystyrene-supported triazolylproline organocatalyst. Green Chem., 2016, 18(12), 3507-3512.
[http://dx.doi.org/10.1039/C6GC00792A]
[44]
Zhao, W.; Zou, J.; Cui, Y. Asymmetric Aldol reaction catalyzed by polyvinyl chloride supported L-proline. Polym. Bull., 2010, 3, 37-43.
[http://dx.doi.org/10.14028/j.cnki.1003-3726.2010.05.001]
[45]
Kristensen, T.E.; Hansen, F.K.; Hansen, T. The selective O-acylation of hydroxyproline as a convenient method for the large-scale preparation of novel proline polymers and amphiphiles. Eur. J. Org. Chem., 2009, 2009(3), 387-395.
[http://dx.doi.org/10.1002/ejoc.200800941]
[46]
Li, X.; Lu, C.; Chen, M.; Hu, Z. Preparation of thermosensitive copolymer supported with L-proline and its catalytic activity for direct asymmetric Aldol reaction in water. Chem. Res Appl., 2015, 27, 1484-1488.http://dx.chinadoi.cn/10.3969/j.issn.1004-1656.2015.10.011
[47]
Li, X.; Chen, M.; Yang, B.; Zhang, S.; Jia, X.; Hu, Z. Combining RAFT precipitation polymerization and surface-initiated RAFT polymerization: an efficient approach to prepare hairy particles—supported proline. RSC Advances, 2014, 4(82), 43278-43285.
[http://dx.doi.org/10.1039/C4RA06176D]
[48]
Li, X.; Yang, B.; Jia, X.; Chen, M.; Hu, Z. Temperature-responsive hairy particle-supported proline for direct asymmetric aldol reaction in water. RSC Advances, 2015, 5(108), 89149-89156.
[http://dx.doi.org/10.1039/C5RA16393E]
[49]
Tang, Y.; Wang, Q.; Wu, L.; Liu, K.; Wang, W.; Shen, Y.; Xue, Y.; Dai, S. L-proline functionalized pH-responsive copolymers as supported organocatalysts for asymmetric aldol reaction in water. React. Funct. Polym., 2020, 150, 104544.
[http://dx.doi.org/10.1016/j.reactfunctpolym.2020.104544]
[50]
Liu, S.; Sun, T.; Yang, D.; Cao, M.; Liang, H. Polyacrylic acid supported TEMPO for selective catalytic oxidation of cellulose: recovered by its pH sensitivity. Cellulose, 2018, 25(10), 5687-5696.
[http://dx.doi.org/10.1007/s10570-018-2012-z]
[51]
Guo, X.; Wang, J.; Li, L.; Pham, D.T.; Clements, P.; Lincoln, S.F.; May, B.L.; Chen, Q.; Zheng, L.; Prud’homme, R.K. Tailoring polymeric hydrogels through cyclodextrin host–guest complexation. Macromol. Rapid Commun., 2010, 31(3), 300-304.
[http://dx.doi.org/10.1002/marc.200900560] [PMID: 21590906]
[52]
List, B.; Lerner, R.A.; Barbas, C.F. Proline-catalyzed direct asymmetric aldol reactions. J. Am. Chem. Soc., 2000, 122(10), 2395-2396.
[http://dx.doi.org/10.1021/ja994280y]
[53]
Nakashima, E.; Yamamoto, H. Asymmetric aldol synthesis: Choice of organocatalyst and conditions. Chem. Asian J., 2017, 12(1), 41-44.
[http://dx.doi.org/10.1002/asia.201601525] [PMID: 27860297]
[54]
List, B.; Pojarliev, P.; Castello, C. Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes. Org. Lett., 2001, 3(4), 573-575.
[http://dx.doi.org/10.1021/ol006976y] [PMID: 11178828]
[55]
Tan, R.; Li, C.; Luo, J.; Kong, Y.; Zheng, W.; Yin, D. An effective heterogeneous l-proline catalyst for the direct asymmetric aldol reaction using graphene oxide as support. J. Catal., 2013, 298, 138-147.
[http://dx.doi.org/10.1016/j.jcat.2012.11.024]

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