Citation:
Zhi Wang, Chun-Yu Wang, Hao-Ran Wang, Hong Zhang, Ya-Lun Su, Teng-Fei Ji, Lei Wang. Lipase-catalyzed Knoevenagel condensation between α, β-unsaturated aldehydes and active methylene compounds[J]. Chinese Chemical Letters,
;2014, 25(05): 802-804.
doi:
10.1016/j.cclet.2014.03.036
-
A simple and efficient Knoevenagel condensation between α,β-unsaturated aldehydes and active methylene compounds is reported. Notably, this condensation can be catalyzed by PPL (lipase from porcine pancreas) with satisfied yields (49%-92%). Moreover, PPL induces moderate Z/E selectivity in the Knoevenagel condensation.
-
-
-
[1]
[1] I. Nobeli, A.D. Favia, J.M. Thornton, Protein promiscuity and its implications for biotechnology, Nat. Biotechnol. 27 (2009) 157-167.
-
[2]
[2] A.B. Majumder, N.G. Ramesh, M.N. Gupta, A lipase catalyzed condensation reaction with a tricyclic diketone: yet another example of biocatalytic promiscuity, Tetrahedron Lett. 50 (2009) 5190-5193.
-
[3]
[3] M.T. Reetz, R. Mondiere, J.D. Carballeira, Enzyme promiscuity: first proteincatalyzed Morita-Baylis-Hillman reaction, Tetrahedron Lett. 48 (2007) 1679- 1681.
-
[4]
[4] M. Svedendahl, K. Hult, P. Berglund, Fast carbon-carbon bond formation by a promiscuous lipase, J. Am. Chem. Soc. 127 (2005) 17988-17989.
-
[5]
[5] X.F. Wei, Q.C. Zheng, T.F. Ji, et al., Addition of diethylzinc to aromatic aldehydes catalyzed by hydrolase, Chin. J. Catal. 30 (2009) 396-400.
-
[6]
[6] M.A. Ibrahim, M.A.M. Abdel-Hamed, N.M. El-Gohary, A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones, J. Braz. Chem. Soc. 22 (2011) 1130-1139.
-
[7]
[7] M. Oguchi, K. Wada, H. Honma, et al., Molecular design, synthesis, and hypoglycemic activity of a series of thiazolidine-2,4-diones, J. Med. Chem. 43 (2000) 3052-3066.
-
[8]
[8] M.S. Malamas, J. Sredy, I. Gunawan, et al., New azolidinediones as inhibitors of protein tyrosine phosphatase lb with antihyperglycemic properties, J. Med. Chem. 43 (2000) 995-1010.
-
[9]
[9] R. Murugan, S. Anbazhagan, S. Sriman Narayanan, Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3 + 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives, Eur. J. Med. Chem. 44 (2009) 3272-3279.
-
[10]
[10] C.B. Yue, A.Q. Mao, Y.Y. Wei, M.J. Lü, Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions, Catal. Commun. 9 (2008) 1571-1574.
-
[11]
[11] G.W. Li, J. Xiao, W.Q. Zhang, Highly efficient Knoevenagel condensation reactions catalyzed by a proline-functionalized polyacrylonitrile fiber, Chin. Chem. Lett. 24 (2013) 52-54.
-
[12]
[12] K.P. Boroujeni, M. Jafarinasab, Polystyrene-supported chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for Knoevenagel condensation, Chin. Chem. Lett. 23 (2012) 1067-1070.
-
[13]
[13] F. Marta, O. Monica, P. Laura, I. Achille, Electrochemically induced Knoevenagel condensation in solvent- and supporting electrolyte-free conditions, Green Chem. 9 (2007) 323-325.
-
[14]
[14] S. Balalaie, N. Nemati, Ammonium acetate-basic alumina catalyzed Knoevenagel condensation under microwave irradiation under solvent-free condition, Synth. Commun. 30 (2000) 869-875.
-
[15]
[15] M. James, A.S. Jennifer, W. Sonja, The ultrasound promoted Knoevenagel condensation of aromatic aldehydes, Tetrahedron Lett. 39 (1998) 8013-8016.
-
[16]
[16] Y.F. Lai, H. Zheng, S.J. Chai, P.F. Zhang, X.Z. Chen, Lipase-catalysed tandem Knoevenagel condensation and esterification with alcohol cosolvents, Green Chem. 12 (2010) 1917-1918.
-
[17]
[17] W. Hua, Z. Guan, X. Deng, Y.H. He, Enzyme catalytic promiscuity: the papaincatalyzed Knoevenagel reaction, Biochimie 94 (2012) 656-661.
-
[18]
[18] L. Wang, J.D. Tai, R. Wang, et al., Enantioselective transesterification of glycidol catalysed by a novel lipase expressed from Bacillus subtilis, Biotechnol. Appl. Biochem. 56 (2010) 1-6.
-
[19]
[19] R. Tian, C.H. Yang, X.F. Wei, et al., Optimization of APE1547-catalyzed enantioselective transesterification of (R/S)-2-methyl-1-butanol in an ionic liquid, Biotechnol. Bioproc. E 16 (2011) 337-342.
-
[20]
[20] Z. Wang, R. Wang, J. Tian, et al., The effect of ultrasound on lipase-catalyzed regioselective acylation of mangiferin in non-aqueous solvents, J. Asian Nat. Prod. Res. 12 (2010) 56-63.
-
[21]
[21] E.N. Xun, J.X. Wang, H. Zhang, et al., Resolution of N-hydroxymethyl vince lactam catalyzed by lipase in organic solvent, J. Chem. Technol. Biotechnol. 88 (2013) 904-909.
-
[22]
[22] A.B. Martins, J.L.R. Friedrich, J.C. Cavalheiro, et al., Improved production of butyl butyrate with lipase from Thermomyces lanuginosus immobilized on styrene- divinylbenzene beads, Bioresour. Technol. 134 (2013) 417-422.
-
[23]
[23] Y.S. Lin, P.Y. Wang, A.C. Wu, S.W. Tsai, Lipase-catalyzed enantioselective resolution of (R,S)-N-2-methylalkanoyl-3-(2-pyridyl)pyrazoles in organic solvents, J. Mol. Catal. B: Enzym. 68 (2011) 245-249.
-
[1]
-
-
-
[1]
Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
-
[2]
Guang-Xu Duan , Queting Chen , Rui-Rui Shao , Hui-Huang Sun , Tong Yuan , Dong-Hao Zhang . Encapsulating lipase on the surface of magnetic ZIF-8 nanosphers with mesoporous SiO2 nano-membrane for enhancing catalytic performance. Chinese Chemical Letters, 2025, 36(2): 109751-. doi: 10.1016/j.cclet.2024.109751
-
[3]
Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
-
[4]
Shicheng Dong , Jun Zhu . Could π-aromaticity cross an unsaturated system to a fully saturated one?. Chinese Chemical Letters, 2024, 35(6): 109214-. doi: 10.1016/j.cclet.2023.109214
-
[5]
Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
-
[6]
Jinli Chen , Shouquan Feng , Tianqi Yu , Yongjin Zou , Huan Wen , Shibin Yin . Modulating Metal-Support Interaction Between Pt3Ni and Unsaturated WOx to Selectively Regulate the ORR Performance. Chinese Journal of Structural Chemistry, 2023, 42(10): 100168-100168. doi: 10.1016/j.cjsc.2023.100168
-
[7]
Longlong Geng , Huiling Liu , Wenfeng Zhou , Yong-Zheng Zhang , Hongliang Huang , Da-Shuai Zhang , Hui Hu , Chao Lv , Xiuling Zhang , Suijun Liu . Construction of metal-organic frameworks with unsaturated Cu sites for efficient and fast reduction of nitroaromatics: A combined experimental and theoretical study. Chinese Chemical Letters, 2024, 35(8): 109120-. doi: 10.1016/j.cclet.2023.109120
-
[8]
Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
-
[9]
Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
-
[10]
Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
-
[11]
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
-
[12]
Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
-
[13]
Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
-
[14]
Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co2P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
-
[15]
Zhaomin Tang , Qian He , Jianren Zhou , Shuang Yan , Li Jiang , Yudong Wang , Chenxing Yao , Huangzhao Wei , Keda Yang , Jiajia Wang . Active-transporting of charge-reversal Cu(Ⅱ)-doped mesoporous silica nanoagents for antitumor chemo/chemodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109742-. doi: 10.1016/j.cclet.2024.109742
-
[16]
Li Li , Fanpeng Chen , Bohang Zhao , Yifu Yu . Understanding of the structural evolution of catalysts and identification of active species during CO2 conversion. Chinese Chemical Letters, 2024, 35(4): 109240-. doi: 10.1016/j.cclet.2023.109240
-
[17]
Ling Fang , Sha Wang , Shun Lu , Fengjun Yin , Yujie Dai , Lin Chang , Hong Liu . Efficient electroreduction of nitrate via enriched active phases on copper-cobalt oxides. Chinese Chemical Letters, 2024, 35(4): 108864-. doi: 10.1016/j.cclet.2023.108864
-
[18]
Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
-
[19]
Jiaqi Lin , Pupu Yang , Yimin Jiang , Shiqian Du , Dongcai Zhang , Gen Huang , Jinbo Wang , Jun Wang , Qie Liu , Miaoyu Li , Yujie Wu , Peng Long , Yangyang Zhou , Li Tao , Shuangyin Wang . Surface decoration prompting the decontamination of active sites in high-temperature proton exchange membrane fuel cells. Chinese Chemical Letters, 2024, 35(11): 109435-. doi: 10.1016/j.cclet.2023.109435
-
[20]
Weiping Xiao , Yuhang Chen , Qin Zhao , Danil Bukhvalov , Caiqin Wang , Xiaofei Yang . Constructing the synergistic active sites of nickel bicarbonate supported Pt hierarchical nanostructure for efficient hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(12): 110176-. doi: 10.1016/j.cclet.2024.110176
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(661)
- HTML views(28)