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Artykuły w czasopismach na temat „Electron-poor alkenes”

Autor: Grafiati

Data publikacji: 30 listopada 2024

Data aktualizacji: 31 lipca 2025

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1

Bower, John F., Timothy P. Aldhous, Raymond W. M. Chung, and Andrew G. Dalling. "Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions." Synthesis 53, no. 17 (2021): 2961–75. http://dx.doi.org/10.1055/s-0040-1720406.

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AbstractStrategies that enable the efficient assembly of complex building blocks from feedstock chemicals are of paramount importance to synthetic chemistry. Building upon the pioneering work of Murai and co-workers in 1993, C–H-activation-based enantioselective hydroarylations of alkenes offer a particularly promising framework for the step- and atom-economical installation of benzylic stereocenters. This short review presents recent intermolecular enantioselective Murai-type alkene hydroarylation methodologies and the mechanisms by which they proceed.1 Introduction2 Enantioselective Hydroary

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2

Hajdók, Imre, Falk Lissner, Martin Nieger, Sabine Strobel, and Dietrich Gudat. "Diphosphination of Electron Poor Alkenes." Organometallics 28, no. 6 (2009): 1644–51. http://dx.doi.org/10.1021/om801179k.

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3

Clennan, Edward L., Jakub P. Sram, Andrea Pace, Katie Vincer, and Sophia White. "Intrazeolite Photooxidations of Electron-Poor Alkenes." Journal of Organic Chemistry 67, no. 11 (2002): 3975–78. http://dx.doi.org/10.1021/jo025657c.

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4

Mieusset, Jean-Luc, Michael Abraham, and Udo H. Brinker. "Carbene−Alkene Complexes between a Nucleophilic Carbene and Electron-Poor Alkenes†." Journal of the American Chemical Society 130, no. 44 (2008): 14634–39. http://dx.doi.org/10.1021/ja8042118.

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5

Dixon, Craig E., Jeffrey A. Cooke, and Kim M. Baines. "The Reaction of Group 14 Dimetallenes with Alkenes: Electron-Poor Alkenes." Organometallics 16, no. 25 (1997): 5437–40. http://dx.doi.org/10.1021/om970638s.

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6

Navarro, Miquel, Alberto Toledo, Sonia Mallet-Ladeira, E. Daiann Sosa Carrizo, Karinne Miqueu та Didier Bourissou. "Versatility and adaptative behaviour of the P^N chelating ligand MeDalphos within gold(i) π complexes". Chemical Science 11, № 10 (2020): 2750–58. http://dx.doi.org/10.1039/c9sc06398f.

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The hemilabile P^N ligand MeDalphos enables access to a wide range of stable gold(i) π-complexes with unbiased alkenes and alkynes, as well as electron-rich alkenes and for the first time electron-poor ones.

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7

Baird, Mark S., Michele E. Gerrard, and Robert J. G. Searle. "Trapping of the tribromomethylanion by electron poor alkenes." Tetrahedron Letters 26, no. 51 (1985): 6353–56. http://dx.doi.org/10.1016/s0040-4039(01)84597-4.

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8

Bonini, Carlo, Maurizio D'Auria, Rachele Ferri, Rachele Pucciariello, and Anna Rita Sabia. "Graft copolymers of lignin with electron poor alkenes." Journal of Applied Polymer Science 90, no. 4 (2003): 1163–71. http://dx.doi.org/10.1002/app.12801.

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9

Ballini, R., L. Barboni, G. Bosica, D. Fiorini, and A. Palmieri. "Synthesis of fine chemicals by the conjugate addition of nitroalkanes to electrophilic alkenes." Pure and Applied Chemistry 78, no. 10 (2006): 1857–66. http://dx.doi.org/10.1351/pac200678101857.

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Several aliphatic nitro compounds have been employed as stabilized carbanions in the conjugate addition to a variety of electron-poor alkenes (Michael reaction). Depending on the nature of the alkene, new carbon-carbon single or double bonds can be generated. However, all the Michael adducts can be efficiently utilized as key building blocks for the synthesis of a huge array of fine chemicals, including homo- and heterocyclic structures.

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10

Inés, Blanca, David Palomas, Sigrid Holle, Sebastian Steinberg, Juan A. Nicasio, and Manuel Alcarazo. "Metal-Free Hydrogenation of Electron-Poor Allenes and Alkenes." Angewandte Chemie International Edition 51, no. 49 (2012): 12367–69. http://dx.doi.org/10.1002/anie.201205348.

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11

Xin, Jing-Rui, Yan-Hong He, and Zhi Guan. "Metal-free aerobic oxidative direct C–H amination of electron-deficient alkenes via photoredox catalysis." Organic Chemistry Frontiers 5, no. 10 (2018): 1684–88. http://dx.doi.org/10.1039/c8qo00161h.

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12

Strappaveccia, Giacomo, Luca Bianchi, Simone Ziarelli, et al. "PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes." Organic & Biomolecular Chemistry 14, no. 14 (2016): 3521–25. http://dx.doi.org/10.1039/c6ob00242k.

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13

Ballini, Roberto, Giovanna Bosica, Dennis Fiorini, Alessandro Palmieri, and Marino Petrini. "Conjugate Additions of Nitroalkanes to Electron-Poor Alkenes: Recent Results." Chemical Reviews 105, no. 3 (2005): 933–72. http://dx.doi.org/10.1021/cr040602r.

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14

Adembri, Giorgio, Angela M. Celli, and Mirella Scotton. "1,3-Dipolar cycloadditions of aryl nitrilimines to electron-poor alkenes." Journal of Heterocyclic Chemistry 25, no. 1 (1988): 249–51. http://dx.doi.org/10.1002/jhet.5570250140.

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15

Ruiz, Javier, Marta P. Gonzalo, Marilín Vivanco та Santiago García-Granda. "Synthesis and derivatization of highly-functionalized λ5-phospholes". Chem. Commun. 50, № 42 (2014): 5597–99. http://dx.doi.org/10.1039/c4cc02089h.

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16

Messire, Gatien, Fabien Massicot, Laura Pascual, Emmanuel Riguet, Jean-Luc Vasse, and Jean-Bernard Behr. "Broadening the reaction scope of unprotected aldoses via their corresponding nitrones: 1,3-dipolar cycloadditions with alkenes." Organic & Biomolecular Chemistry 18, no. 29 (2020): 5708–25. http://dx.doi.org/10.1039/d0ob01350a.

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Condensation reactions of unprotected tetroses and pentoses with hydroxylamines afforded nitrones, which were easily converted to densely functionalized isoxazolidines in the presence of electron-poor alkenes.

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17

Liu, Kun, Dirk Leifert, and Armido Studer. "Cooperative triple catalysis enables regioirregular formal Mizoroki–Heck reactions." Nature Synthesis 1, no. 7 (2022): 565–75. http://dx.doi.org/10.1038/s44160-022-00101-9.

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AbstractThe Mizoroki–Heck reaction between alkenes and aryl halides represents one of the most important methods for C−C bond formation in synthetic chemistry. Governed by their electronic and steric nature, alkenes are generally arylated with high regioselectivity, which conversely hampers diversity, in particular, if the regioirregular isomer is targeted. Usually, electron-poor alkenes selectively afford the corresponding β-coupled products, and achieving the opposite regioselectivity to obtain their α-arylated congeners is highly challenging. It would be desirable to access the irregular α-

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18

Cermenati, Laura, Maurizio Fagnoni, and Angelo Albini. "TiO2-photocatalyzed reactions of some benzylic donors." Canadian Journal of Chemistry 81, no. 6 (2003): 560–66. http://dx.doi.org/10.1139/v03-048.

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TiO2-photocatalyzed oxidation of toluene (1a), benzyltrimethylsilane (1b), and 4-methoxybenzyltrimethylsilane (1c) has been carried out in acetonitrile under oxygen, under nitrogen, and in the presence of electrophilic alkenes under various conditions (using Ag2SO4 as electron acceptor, adding 2.5% H2O, changing solvent to CH2Cl2). Benzyl radicals, formed via electron transfer and fragmentation, are trapped. A good material balance is often obtained. The overall efficiency of the process depends on the donor Eox, on the rate of fragmentation of the radical cation, and on the acceptor present (

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19

Huval, C. C., K. M. Church, and D. A. Singleton. "Free-Radical Mediated [3 + 2] Methylenecyclopentane Annulations of Electron-Poor Alkenes." Synlett 1994, no. 04 (1994): 273–74. http://dx.doi.org/10.1055/s-1994-22825.

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20

Ines, Blanca, David Palomas, Sigrid Holle, Sebastian Steinberg, Juan A. Nicasio, and Manuel Alcarazo. "ChemInform Abstract: Metal-Free Hydrogenation of Electron-Poor Allenes and Alkenes." ChemInform 44, no. 22 (2013): no. http://dx.doi.org/10.1002/chin.201322072.

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21

Shukla, Prashant, Manorama Singh, Vijai K. Rai, and Ankita Rai. "Regioselective installation of enolizable ketones and unprotected mercaptoacetic acid into olefins using GO as a phase transfer catalyst." New Journal of Chemistry 46, no. 7 (2022): 3297–304. http://dx.doi.org/10.1039/d1nj05870c.

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Unprecedented regioselective conjugate addition of enolizable ketones and unprotected mercaptoacetic acid to electron poor alkenes using GO as a phase transfer catalyst is reported in excellent yield of products (up to 92%) and recyclability of the catalyst up to five times.

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22

Baker, S. Richard, Karen Goodall, Andrew F. Parsons та Michelle Wilson. "Tributyltin Hydride-Mediated Tandem reactions of Dehydroalanines Leading to α-Substituted Pyroglutamates". Journal of Chemical Research 2000, № 7 (2000): 312–13. http://dx.doi.org/10.3184/030823400103167651.

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Tributyltin hydride-mediated cyclisation of dehydroalanines produces an intermediate captodative radical, which can be trapped by reaction with oxygen- or carbon-centred radicals or (principally) electron-poor alkenes, to provide a quick approach to a variety of α-substituted pyroglutamates.

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23

Rocchetti, Maria Teresa, Vincenzo Fino, Vito Capriati, Saverio Florio, and Renzo Luisi. "Michael Addition of Chloroalkyloxazolines to Electron-Poor Alkenes: Synthesis of Heterosubstituted Cyclopropanes†." Journal of Organic Chemistry 68, no. 4 (2003): 1394–400. http://dx.doi.org/10.1021/jo026661r.

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24

Swager, Timothy, and Cagatay Dengiz. "Homoconjugated and Spiro Push–Pull Systems: Cycloadditions of Naphtho- and Anthradiquinones with Electron-Rich Alkynes." Synlett 28, no. 12 (2017): 1427–31. http://dx.doi.org/10.1055/s-0036-1588771.

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We report the synthesis and characterization of three new classes of push–pull chromophores using [2+2]-cycloaddition reactions of electron-rich alkynes and electron-poor alkenes. Previous investigations have focused on the reactions of cyano-substituted electron acceptors. This study demonstrates that cyano-free electron acceptors, naphtho- and anthradiquinones, can also be used to access extended push–pull systems. The effects of the structural changes on the spectroscopic and electronic properties were investigated by UV/vis spectroscopy. Structures were confirmed by X-ray and NMR analysis

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25

D’Auria, Maurizio, Rocco Racioppi, Orazio Attanasi, and Fabio Mantellini. "Unusual [4+2]-Cycloaddition Reaction between Electron-Poor 1,2-Diaza-1,3-dienes and Electron-Poor Alkenes: Useful Entry to Novel Tetrahydropyridazines." Synlett 2010, no. 09 (2010): 1363–66. http://dx.doi.org/10.1055/s-0029-1219834.

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26

Reekie, Tristan A., Etienne J. Donckele, Laurent Ruhlmann, Corinne Boudon, Nils Trapp, and François Diederich. "Ester-Substituted Electron-Poor Alkenes for Cycloaddition-Retroelectrocyclization (CA-RE) and Related Reactions." European Journal of Organic Chemistry 2015, no. 33 (2015): 7264–75. http://dx.doi.org/10.1002/ejoc.201501085.

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27

Attanasi, Orazio, Luca Bianchi, Maurizio D’Auria, Fabio Mantellini, and Rocco Racioppi. "Novel Tetrahydropyridazines by Unusual Aza-Diels-Alder Reaction of Electron-poor 1,2-Diaza-1,3-dienes with Electron-poor Alkenes Under Solvent Free Conditions." Current Organic Synthesis 10, no. 4 (2013): 631–39. http://dx.doi.org/10.2174/1570179411310040006.

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28

D'Auria, Maurizio, Rocco Racioppi, Orazio A. Attanasi, and Fabio Mantellini. "ChemInform Abstract: Unusual [4 + 2]-Cycloaddition Reaction Between Electron-Poor 1,2-Diaza-1,3-dienes and Electron-Poor Alkenes: Useful Entry to Novel Tetrahydropyridazines." ChemInform 41, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.201041145.

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29

Campbell, Matthew J., Patrick D. Pohlhaus, Geanna Min, Kohsuke Ohmatsu, and Jeffrey S. Johnson. "An “Anti-Baldwin” 3-Exo-DigCyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes." Journal of the American Chemical Society 130, no. 29 (2008): 9180–81. http://dx.doi.org/10.1021/ja803553a.

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30

Lattanzi, Alessandra, та Alessio Russo. "Asymmetric Oxidations of Electron-Poor Alkenes Promoted by the β-Amino Alcohol/TBHP System". Synthesis 2009, № 09 (2009): 1551–56. http://dx.doi.org/10.1055/s-0029-1216638.

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31

Kowalczyk, Rafał, Aleksandra J. Wierzba, Przemysław J. Boratyński, and Julia Bąkowicz. "Enantioselective conjugate addition of aliphatic thiols to divergently activated electron poor alkenes and dienes." Tetrahedron 70, no. 35 (2014): 5834–42. http://dx.doi.org/10.1016/j.tet.2014.06.035.

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32

HUVAL, C. C., K. M. CHURCH, and D. A. SINGLETON. "ChemInform Abstract: Free-Radical Mediated (3 + 2)Methyleneccylopentane Annulations of Electron-Poor Alkenes (II)." ChemInform 25, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199452085.

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33

Marinetti, Angela, and Fran�ois Mathey. "[2 + 2] Cycloadditions between electron-poor phospha-alkene complexes and electron-rich alkenes or alkynes, a new route to phosphetane and 1,2-dihydrophosphete rings." Journal of the Chemical Society, Chemical Communications, no. 2 (1990): 153. http://dx.doi.org/10.1039/c39900000153.

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34

Mamantov, Andrew. "Halocarbenes May Deplete Atmospheric Ozone." Progress in Reaction Kinetics and Mechanism 42, no. 4 (2017): 307–33. http://dx.doi.org/10.3184/146867817x14954764850360.

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Photooxidation of tetrachloroethylene (PERC) and trichloroethylene (TCE) in simulated tropospheric smog chamber studies occurs with a time delay, accelerating simultaneous decreasing O3/chlorinated ethylene (CE) concentrations along with increasing CCl2O, which is attributed to CCl2 in the case of PERC and CCl2 or CHCl for TCE. The carbenes, chlorinated acetyl chlorides and CCl2O products may result from the rearrangement of the oxidised and/or excited oxidised CE, e.g. an epoxide. Analyses indicate scavenging experiments have not proved the existence of Cl atoms as being responsible for chlor

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35

Choi, Anthony, Rebecca M. Morley, and Iain Coldham. "Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts." Beilstein Journal of Organic Chemistry 15 (July 3, 2019): 1480–84. http://dx.doi.org/10.3762/bjoc.15.149.

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Quinolinium salts, Q+-CH2-CO2Me Br− and Q+-CH2-CONMe2 Br− (where Q = quinoline), were prepared from quinolines. Deprotonation of these salts with triethylamine promoted the reaction of the resulting quinolinium ylides (formally azomethine ylides) with electron-poor alkenes by conjugate addition followed by cyclization or by [3 + 2] dipolar cycloaddition. The pyrroloquinoline products were formed as single regio- and stereoisomers. These could be converted to other derivatives by Suzuki–Miyaura coupling, reduction or oxidation reactions.

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36

Maji, Kakoli, Pramod Rai, and Biplab Maji. "Visible‐Light Mediated Metal‐Free Cross‐Electrophile Coupling of Isatin Derivatives with Electron‐Poor Alkenes." Asian Journal of Organic Chemistry 10, no. 7 (2021): 1708–12. http://dx.doi.org/10.1002/ajoc.202100308.

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37

Ramazani, Ali, Abbas Azizian, Maryam Bandpey, and Nader Noshiranzadeh. "One-Step Synthesis of Electron-Poor Alkenes from Triphenylphosphine, Acetylenic Esters, 2,2,2-Trichloroethanol, and Ninhydrin." Phosphorus, Sulfur, and Silicon and the Related Elements 181, no. 12 (2006): 2731–34. http://dx.doi.org/10.1080/10426500600864437.

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38

Rostoll-Berenguer, Jaume, Gonzalo Blay, José R. Pedro, and Carlos Vila. "Photocatalytic Giese Addition of 1,4-Dihydroquinoxalin-2-ones to Electron-Poor Alkenes Using Visible Light." Organic Letters 22, no. 20 (2020): 8012–17. http://dx.doi.org/10.1021/acs.orglett.0c02953.

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39

Pan, Yang, Zhenyu Sheng, Xiaodong Ye, et al. "Photochemistry of quinoxaline derivatives and mechanism of the triplet state quenching by electron-poor alkenes." Journal of Photochemistry and Photobiology A: Chemistry 174, no. 2 (2005): 98–105. http://dx.doi.org/10.1016/j.jphotochem.2005.02.017.

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40

Vijender, Medamoni, P. Kishore, and B. Satyanarayana. "Cadmium Chloride (CdCl2): An Efficient Catalyst for Conjugate Addition of Amines to Electron‐Poor Alkenes." Synthetic Communications 37, no. 4 (2007): 589–92. http://dx.doi.org/10.1080/00397910601055115.

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41

Qrareya, Hisham, Daniele Dondi, Davide Ravelli, and Maurizio Fagnoni. "Decatungstate-Photocatalyzed Si−H/C−H Activation in Silyl Hydrides: Hydrosilylation of Electron-Poor Alkenes." ChemCatChem 7, no. 20 (2015): 3350–57. http://dx.doi.org/10.1002/cctc.201500562.

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42

Palacios, Francisco, Itziar Perez de Heredia, and Gloria Rubiales. "Synthesis and Reactivity of Electron-Poor 2-Azadienes. [4 + 2] Cycloaddition Reactions with Alkenes and Enamines." Journal of Organic Chemistry 60, no. 8 (1995): 2384–90. http://dx.doi.org/10.1021/jo00113a017.

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43

Goretti, Marta, Chiara Ponzoni, Elisa Caselli, et al. "Biotransformation of electron-poor alkenes by yeasts: Asymmetric reduction of (4S)-(+)-carvone by yeast enoate reductases." Enzyme and Microbial Technology 45, no. 6-7 (2009): 463–68. http://dx.doi.org/10.1016/j.enzmictec.2009.09.004.

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44

Kowalczyk, Rafal, Aleksandra J. Wierzba, Przemyslaw J. Boratynski, and Julia Bakowicz. "ChemInform Abstract: Enantioselective Conjugate Addition of Aliphatic Thiols to Divergently Activated Electron Poor Alkenes and Dienes." ChemInform 46, no. 4 (2015): no. http://dx.doi.org/10.1002/chin.201504081.

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Rodríguez-Flórez, Lesly V., María González-Marcos, Eduardo García-Mingüens та ін. "Phosphine Catalyzed Michael-Type Additions: The Synthesis of Glutamic Acid Derivatives from Arylidene-α-amino Esters". Molecules 29, № 2 (2024): 342. http://dx.doi.org/10.3390/molecules29020342.

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The reaction of arylidene-α-amino esters with electrophilic alkenes to yield Michael-type addition compounds is optimized using several phosphines as organocatalysts. The transformation is very complicated due to the generation of several final compounds, including those derived from the 1,3-dipolar cycloadditions. For this reason, the selection of the reaction conditions is a very complex task and the slow addition of the acrylic system is very important to complete the process. The study of the variation in the structural components of the starting imino ester is performed as well as the exp

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46

Ganis, Paolo, Ida Orabona, Francesco Ruffo, and Aldo Vitagliano. "The First Class of Square-Planar Platinum(II) Complexes Containing Electron-Poor Alkenes. Rare Insertion of an Alkene into a Pt−Alkyl Bond†." Organometallics 17, no. 12 (1998): 2646–50. http://dx.doi.org/10.1021/om9800750.

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47

Pizzo, Erika, Paolo Sgarbossa, Alessandro Scarso, Rino A. Michelin, and Giorgio Strukul. "Second-Generation Electron-Poor Platinum(II) Complexes as Efficient Epoxidation Catalysts for Terminal Alkenes with Hydrogen Peroxide." Organometallics 25, no. 12 (2006): 3056–62. http://dx.doi.org/10.1021/om060194c.

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48

Qrareya, Hisham, Daniele Dondi, Davide Ravelli, and Maurizio Fagnoni. "ChemInform Abstract: Decatungstate-Photocatalyzed Si-H/C-H Activation in Silyl Hydrides: Hydrosilylation of Electron-Poor Alkenes." ChemInform 47, no. 9 (2016): no. http://dx.doi.org/10.1002/chin.201609058.

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PALACIOS, F., I. PEREZ DE HEREDIA, and G. RUBIALES. "ChemInform Abstract: Synthesis and Reactivity of Electron-Poor 2-Azadienes. (4 + 2) Cycloaddition Reactions with Alkenes and Enamines." ChemInform 26, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199536043.

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50

Vinokurov, Nikolai, Anna Michrowska, Anna Szmigielska, et al. "Homo- and Cross-Olefin Metathesis Coupling of Vinylphosphane Oxides and Electron-Poor Alkenes: Access to P-Stereogenic Dienophiles." Advanced Synthesis & Catalysis 348, no. 7-8 (2006): 931–38. http://dx.doi.org/10.1002/adsc.200505463.

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