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Journal articles on the topic 'Asymmetric Henry Reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Boruwa, Joshodeep, Naminita Gogoi, Partha Pratim Saikia, and Nabin C. Barua. "Catalytic asymmetric Henry reaction." Tetrahedron: Asymmetry 17, no. 24 (2006): 3315–26. http://dx.doi.org/10.1016/j.tetasy.2006.12.005.

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2

Griengl, H., T. Purkarthofer, K. Gruber, et al. "Biocatalytic Asymmetric Henry Reaction." Synfacts 2006, no. 7 (2006): 0723. http://dx.doi.org/10.1055/s-2006-941912.

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3

Marcelli, Tommaso, Richard N. S. van der Haas, Jan H. van Maarseveen, and Henk Hiemstra. "Asymmetric Organocatalytic Henry Reaction." Angewandte Chemie International Edition 45, no. 6 (2006): 929–31. http://dx.doi.org/10.1002/anie.200503724.

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4

Marcelli, Tommaso, Richard N. S. van der Haas, Jan H. van Maarseveen, and Henk Hiemstra. "Asymmetric Organocatalytic Henry Reaction." Angewandte Chemie 118, no. 6 (2006): 943–45. http://dx.doi.org/10.1002/ange.200503724.

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5

Yamamoto, Hisashi, and Susumu Oda. "Copper-Catalyzed Asymmetric Henry Reaction." Synfacts 8, no. 12 (2012): 1335. http://dx.doi.org/10.1055/s-0032-1317598.

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6

An, Zhe, Lifeng Chen, Yitao Jiang, and Jing He. "Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline." Catalysts 9, no. 9 (2019): 713. http://dx.doi.org/10.3390/catal9090713.

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Heterogeneous synergistic catalysis by SBA-15 immobilized chiral amines catalysts has promoted efficient aza-Michael–Henry tandem reaction for the synthesis of chiral 3-Nitro-1,2-Dihydroquinoline. Final products in the asymmetric aza-Michael–Henry cascade reactions between 2-aminobenzaldehyde and β-nitrostyrolene were afforded in a yield of 85% and an enantiomeric excess (ee) value of 98% on (S)-(–)-2-aminomethyl-1-ethylpyrrolidine immobilized SBA-15. SBA-15-AEP catalyst has been also extended to the asymmetric aza-Michael–Henry cascade reaction of substituted R1-2-aminobenzaldehyde and R2-sub

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7

Gao, Feifeng, Jiang Zhu, Yong Tang, Minzhi Deng, and Changtao Qian. "Asymmetric aza-Henry reaction ofN-tosyl imine." Chirality 18, no. 9 (2006): 741–45. http://dx.doi.org/10.1002/chir.20315.

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8

Halder, Mita, Piyali Bhanja, Md Mominul Islam, Asim Bhaumik, and Sk Manirul Islam. "Chiral copper-salen complex grafted over functionalized mesoporous silica as an efficient catalyst for asymmetric Henry reactions and synthesis of the potent drug (R)-isoproterenol." New Journal of Chemistry 42, no. 14 (2018): 11896–904. http://dx.doi.org/10.1039/c8nj01745j.

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A new chiral Cu(ii)@AFS-1 catalyzed asymmetric Henry reaction (ee = 94%, yield 96%) and diastereoselective Henry reaction have been reported. Additionally, drug (R)-(−)-isoproterenol was synthesized using this protocol.

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9

Otevrel, Jan, David Svestka, and Pavel Bobal. "Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones." Organic & Biomolecular Chemistry 17, no. 21 (2019): 5244–48. http://dx.doi.org/10.1039/c9ob00884e.

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10

Ran, De-qiang, Tian-hua Shen, Xiao-cong Zhou, et al. "Asymmetric henry reaction catalyzed by chiral schiff base." Russian Journal of Organic Chemistry 49, no. 6 (2013): 849–52. http://dx.doi.org/10.1134/s1070428013060080.

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11

Uraguchi, Daisuke, Sawako Sakaki, and Takashi Ooi. "Chiral Tetraaminophosphonium Salt-Mediated Asymmetric Direct Henry Reaction." Journal of the American Chemical Society 129, no. 41 (2007): 12392–93. http://dx.doi.org/10.1021/ja075152+.

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12

Zhang, Sheng, Yanan Li, Youguo Xu, and Zhiyong Wang. "Recent progress in copper catalyzed asymmetric Henry reaction." Chinese Chemical Letters 29, no. 6 (2018): 873–83. http://dx.doi.org/10.1016/j.cclet.2017.10.001.

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13

Torres-Werlé, Maria, Adela Nano, Aline Maisse-François, and Stéphane Bellemin-Laponnaz. "Asymmetric benzoylation and Henry reaction using reusable polytopic bis(oxazoline) ligands and copper(ii)." New J. Chem. 38, no. 10 (2014): 4748–53. http://dx.doi.org/10.1039/c4nj00653d.

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Multitopic bis(oxazoline)-based chiral ligands are associated with copper to generate catalysts for the asymmetric benzoylation of meso-hydrobenzoin, the kinetic resolution of rac-hydrobenzoin and the asymmetric Henry reaction.

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14

Gan, Changsheng. "Asymmetric nitroaldol reaction with a chiral copper complex derived from D-tartaric acid." Canadian Journal of Chemistry 86, no. 3 (2008): 261–63. http://dx.doi.org/10.1139/v08-012.

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A novel catalytic enantioselective Henry reaction has been developed using a tetradentate copper complex derived from D-tartaric acid to give β-nitroalkanols in moderate to high enantioselectivities.Key words: Henry reaction, D-tartaric acid, enantioselective, β-nitroalkanols.

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15

Tanaka, Koichi, Tomoharu Iwashita, Erika Yoshida, et al. "Solvent-dependent strong asymmetric amplification in the catalytic enantioselective Henry reaction using the trans-N,N′-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine-CuCl2 complex." Chemical Communications 51, no. 37 (2015): 7907–10. http://dx.doi.org/10.1039/c5cc02302e.

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16

Shou, Haowen, Zhaoting He, Gang Peng, Weike Su, and Jingbo Yu. "Two approaches for the synthesis of levo-praziquantel." Organic & Biomolecular Chemistry 19, no. 20 (2021): 4507–14. http://dx.doi.org/10.1039/d1ob00453k.

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Two pathways for the preparation of levo-praziquantel are herein reported, which involves mechanochemical (asymmetric) aza-Henry/acylation reaction, hydrogenation reaction, (chiral resolution) and solvent-free acylation-ring closing reaction.

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17

Liu, Mouxiong, Dongdong Gui, Ping Deng, and Hui Zhou. "Asymmetric Henry Reaction of 2-Acylpyridine N-Oxides Catalyzed by a Ni-Aminophenol Sulfonamide Complex: An Unexpected Mononuclear Catalyst." Molecules 24, no. 8 (2019): 1471. http://dx.doi.org/10.3390/molecules24081471.

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The asymmetric Henry reaction of 2-acylpyridine N-oxide remains a challenge as N-oxides generally act as competitive catalyst inhibitors or displace activating ligands. A novel variable yield (up to 99%) asymmetric Henry reaction of 2-acypyridine N-oxides catalyzed by a Ni-aminophenol sulfonamide complex with good to excellent enantioselectivity (up to 99%) has been developed. Mechanistic studies suggest that the unique properties of the electron-pairs of N-oxides for complexation with Ni makes the unexpected mononuclear complex, rather than the previously reported dinuclear complex, the activ

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18

He, Feilong, Guanghui Chen, Junxia Yang та ін. "Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides". RSC Advances 8, № 17 (2018): 9414–22. http://dx.doi.org/10.1039/c8ra00552d.

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19

M.F. Phillips, Ana. "Recent Advances on the Organocatalytic Asymmetric Aza-Henry Reaction." Current Organocatalysis 3, no. 3 (2016): 222–42. http://dx.doi.org/10.2174/2213337202666150908210627.

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20

Otevrel, Jan, and Pavel Bobal. "Diamine-Tethered Bis(thiourea) Organocatalyst for Asymmetric Henry Reaction." Journal of Organic Chemistry 82, no. 16 (2017): 8342–58. http://dx.doi.org/10.1021/acs.joc.7b00079.

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21

Gao, Yong-guang, Na Chen, Hua-jiang Wu, and Xin-sheng Li. "Chiral copper-Schiff base catalyst for asymmetric henry reaction." Russian Journal of Organic Chemistry 43, no. 12 (2007): 1754–56. http://dx.doi.org/10.1134/s1070428007120020.

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22

Palomo, Claudio, Mikel Oiarbide, and Antonia Mielgo. "Unveiling Reliable Catalysts for the Asymmetric Nitroaldol (Henry) Reaction." Angewandte Chemie International Edition 43, no. 41 (2004): 5442–44. http://dx.doi.org/10.1002/anie.200460506.

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23

Palomo, Claudio, Mikel Oiarbide, and Antonio Laso. "Recent Advances in the Catalytic Asymmetric Nitroaldol (Henry) Reaction." European Journal of Organic Chemistry 2007, no. 16 (2007): 2561–74. http://dx.doi.org/10.1002/ejoc.200700021.

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24

Marcelli, Tommaso, Richard N. S. van der Haas, Jan H. van Maarseveen, and Henk Hiemstra. "Titelbild: Asymmetric Organocatalytic Henry Reaction (Angew. Chem. 6/2006)." Angewandte Chemie 118, no. 6 (2006): 851. http://dx.doi.org/10.1002/ange.200690021.

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25

Guo, Jun, and Jincheng Mao. "Asymmetric Henry reaction catalyzed by bifunctional copper-based catalysts." Chirality 21, no. 6 (2009): 619–27. http://dx.doi.org/10.1002/chir.20661.

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26

Piccionello, A. Palumbo, P. Pierro, A. Accardo, S. Buscemi, and A. Pace. "Concise asymmetric synthesis of Linezolid through catalyzed Henry reaction." RSC Advances 3, no. 47 (2013): 24946. http://dx.doi.org/10.1039/c3ra45186k.

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27

Ooi, T., D. Uraguchi, and S. Nakamura. "Asymmetric Direct Henry Reaction of Ynals Catalyzed by Iminophosphorane." Synfacts 2010, no. 11 (2010): 1309. http://dx.doi.org/10.1055/s-0030-1258782.

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28

Kattuboina, Adiseshu, Parminder Kaur, Teng Ai, and Guigen Li. "Chiral N-Phosphonyl Imine Chemistry: Asymmetric Aza-Henry Reaction." Chemical Biology & Drug Design 71, no. 3 (2008): 216–23. http://dx.doi.org/10.1111/j.1747-0285.2008.00633.x.

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29

Mei, Luo, Yin Hao, Zhang Jia Hai, Hu Ke Liang, and Pang Wen Min. "Asymmetric Henry reaction catalyzed by oxazolinyl Cu(II) complexes." Research on Chemical Intermediates 35, no. 1 (2009): 123–36. http://dx.doi.org/10.1007/s11164-008-0008-2.

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30

Chen, Wei, Zhao-Hui Zhou та Hong-Bin Chen. "Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction". Organic & Biomolecular Chemistry 15, № 6 (2017): 1530–36. http://dx.doi.org/10.1039/c6ob02569b.

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31

Vijaya, Ponmuthu Kottala, Sepperumal Murugesan, and Ayyanar Siva. "Highly enantioselective asymmetric Henry reaction catalyzed by novel chiral phase transfer catalysts derived from cinchona alkaloids." Organic & Biomolecular Chemistry 14, no. 42 (2016): 10101–9. http://dx.doi.org/10.1039/c6ob01687a.

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Newly synthesized CPTCs are applied in the asymmetric Henry reaction to a wide range of aldehydes under mild reaction conditions, and we obtained higher chemical yields and an excellent enantiomeric excess.

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32

Deka, Jogesh, L. Satyanarayana, G. V. Karunakar, Pradip Kr Bhattacharyya, and Kusum K. Bania. "Chiral modification of copper exchanged zeolite-Y with cinchonidine and its application in the asymmetric Henry reaction." Dalton Transactions 44, no. 48 (2015): 20949–63. http://dx.doi.org/10.1039/c5dt03630e.

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33

Zhou, Jing, Li-Juan Bai, Guo-Juan Liang, Qi-Gui Xu, Li-Ping Zhou та Hui Zhou. "Organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction of ortho-hydroxyphenyl-substituted p-QMs with α-nitroketones". Organic & Biomolecular Chemistry 18, № 14 (2020): 2641–45. http://dx.doi.org/10.1039/d0ob00397b.

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Novel organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction is developed to give new chiral 2-(1-(4-hydroxyphenyl)ethyl)phenols with good yields and excellent enantioselectivities under mild reaction conditions.

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34

Kumar, Akshay, Jasneet Kaur, Swapandeep Singh Chimni, and Amanpreet Kaur Jassal. "Organocatalytic enantioselective aza-Henry reaction of ketimines derived from isatins: access to optically active 3-amino-2-oxindoles." RSC Adv. 4, no. 47 (2014): 24816–19. http://dx.doi.org/10.1039/c4ra00902a.

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35

Pellegrino, Sara, Giorgio Facchetti, Alessandro Contini, et al. "Ctr-1 Mets7 motif inspiring new peptide ligands for Cu(i)-catalyzed asymmetric Henry reactions under green conditions." RSC Advances 6, no. 75 (2016): 71529–33. http://dx.doi.org/10.1039/c6ra16255j.

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36

Rossetti, Arianna, Stefano Landoni, Fiorella Meneghetti, et al. "Application of chiral bi- and tetra-dentate bispidine-derived ligands in the copper(ii)-catalyzed asymmetric Henry reaction." New Journal of Chemistry 42, no. 14 (2018): 12072–81. http://dx.doi.org/10.1039/c8nj01930d.

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37

Xu, Shanshan, Yuhan Zhou, and Jingping Qu. "Asymmetric Henry Reaction Catalyzed by CuOTf/NNN Tridentate Pincer Ligand." Chinese Journal of Organic Chemistry 32, no. 6 (2012): 1131. http://dx.doi.org/10.6023/cjoc1108303.

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38

Ni, Bukuo, and Junpeng He. "Highly asymmetric Henry reaction catalyzed by chiral copper(II) complexes." Tetrahedron Letters 54, no. 6 (2013): 462–65. http://dx.doi.org/10.1016/j.tetlet.2012.11.053.

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39

Guo, Zong-Liang, Shi Zhong, Yong-Bo Li, and Gui Lu. "Chiral 1,1′-binaphthylazepine derived amino alcohol catalyzed asymmetric Henry reaction." Tetrahedron: Asymmetry 22, no. 2 (2011): 238–45. http://dx.doi.org/10.1016/j.tetasy.2011.01.026.

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40

Zheng, Bing, Min Wang, Zhiyuan Li, et al. "Asymmetric Henry reaction catalyzed by a Zn–amino alcohol system." Tetrahedron: Asymmetry 22, no. 11 (2011): 1156–60. http://dx.doi.org/10.1016/j.tetasy.2011.06.032.

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41

El-Asaad, Bilal, Estelle Métay, Iyad karamé, and Marc Lemaire. "Chiral N -arylated diamine – Copper complexes catalyzed asymmetric Henry reaction." Molecular Catalysis 435 (July 2017): 76–81. http://dx.doi.org/10.1016/j.mcat.2017.03.017.

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42

Gogoi, Naminita, Joshodeep Boruwa, and Nabin C. Barua. "A total synthesis of (−)-bestatin using Shibasaki’s asymmetric Henry reaction." Tetrahedron Letters 46, no. 44 (2005): 7581–82. http://dx.doi.org/10.1016/j.tetlet.2005.08.153.

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43

Sohtome, Yoshihiro, Yuichi Hashimoto, and Kazuo Nagasawa. "Guanidine-Thiourea Bifunctional Organocatalyst for the Asymmetric Henry (Nitroaldol) Reaction." Advanced Synthesis & Catalysis 347, no. 11-13 (2005): 1643–48. http://dx.doi.org/10.1002/adsc.200505148.

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44

Trost, Barry M., and Vince S. C. Yeh. "A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction." Angewandte Chemie 114, no. 5 (2002): 889–91. http://dx.doi.org/10.1002/1521-3757(20020301)114:5<889::aid-ange889>3.0.co;2-8.

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45

Zhou, Hui, Yajun Liu, Ping Deng, Xiangyang Li, and Yan Xiong. "Asymmetric Henry Reaction Catalyzed by a Chiral Dinuclear Nickel Complex." Synlett 25, no. 12 (2014): 1735–38. http://dx.doi.org/10.1055/s-0033-1339112.

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46

Bulut, Adnan, Ayhan Aslan, and Özdemir Dogan. "Catalytic Asymmetric Nitroaldol (Henry) Reaction with a Zinc-Fam Catalyst." Journal of Organic Chemistry 73, no. 18 (2008): 7373–75. http://dx.doi.org/10.1021/jo8010073.

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47

Koskinen, Ari, Markku Oila, and Jan Tois. "A New Application for PyOX-Ligands: The Asymmetric Henry Reaction." Letters in Organic Chemistry 5, no. 1 (2008): 11–16. http://dx.doi.org/10.2174/157017808783330216.

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48

Ran, De-qiang, Tian-hua Shen, Xiao-cong Zhou, et al. "ChemInform Abstract: Asymmetric Henry Reaction Catalyzed by Chiral Schiff Base." ChemInform 44, no. 51 (2013): no. http://dx.doi.org/10.1002/chin.201351069.

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49

Dimroth, J., and M. Weck. "Co–salen complexes as catalysts for the asymmetric Henry reaction – reversed enantioselectivity through simple ligand modification." RSC Advances 5, no. 37 (2015): 29108–13. http://dx.doi.org/10.1039/c4ra16931j.

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Derivatives of Co-salen catalysts were tested in the asymmetric Henry reaction. Cyclic oligomers displayed a higher catalytic activity than their monomeric counterparts, and reduced Schiff-base versions showed a reversed enantioselectivity.

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50

Biegasiewicz, Kyle F., Michelle L. Ingalsbe, Jeffrey D. St. Denis, et al. "Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions." Beilstein Journal of Organic Chemistry 8 (October 22, 2012): 1814–18. http://dx.doi.org/10.3762/bjoc.8.207.

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Recently, a novel chiral cubane-based Schiff base ligand was reported to yield modest enantioselectivity in the Henry reaction. To further explore the utility of this ligand in other asymmetric organic transformations, we evaluated its stereoselectivity in cyclopropanation and Michael addition reactions. Although there was no increase in stereocontrol, upon computational evaluation using both M06L and B3LYP calculations, it was revealed that a pseudo six-membered ring exists, through H-bonding of a cubyl hydrogen to the copper core. This decreases the steric bulk above the copper center and li

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