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Journal articles on the topic 'Michael's Addition'

Author: Grafiati

Published: 23 September 2022

Last updated: 28 January 2023

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1

Urosevic, Jovica, Sasa Drmanic, Jasmina Nikolic, Ivan Juranic, and Bratislav Jovanovic. "Structure-reactivity correlation for the kinetics of the reaction of substituted 4-phenyl-1,4-dihydropyridines formation." Journal of the Serbian Chemical Society 78, no. 12 (2013): 1963–73. http://dx.doi.org/10.2298/jsc131120139u.

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Quantitative structure-reactivity correlations for the kinetics of the Hantzsch's synthesis of substituted 4-phenyl-1,4-dihydropyridines in the reaction between ethyl m- and p-substituted benzylidene acetoacetate and enamine has been studied. The reaction kinetics was followed using spectrophotometric measurements. It was found that the reaction correspond to the second-order kinetics. Quantitative structure-reactivity correlations of log k with the corresponding substituent constants (s,s+,sI and sR+) using Hammett and extended Hammett equation (DSP equation). They show linear relationship with positive values of reaction constants (r). The obtained data were processed by the linear regression analysis. It is confirmed that Michael's addition of enamine to benzylidene represents the slow step of the reaction with high positive charge at the benzylidene molecule. MO calculations were performed and they were also in agreement with the conclusions derived from structure-reactivity correlations.

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2

BOZKURT, Selahattin. "Asimetrik Michael Katılma Tepkimesi için Prolin bazlı β-Hidroksiamit Organokatalizörü". Afyon Kocatepe Üniversitesi Uluslararası Mühendislik Teknolojileri ve Uygulamalı Bilimler Dergisi 5, № 1 (2022): 13–17. http://dx.doi.org/10.53448/akuumubd.1111800.

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Applications of chiral organocatalysts in reaction types capable of forming C-C bonds, such as Michael addition, are one of the important research areas of recent years. One of the best examples of Michael addition, one of the important works of organic reaction types, is the reaction of nitroolefins with ketones in the presence of organocatalysts. In this study, L-proline-based amide derivative was synthesized with moderate yield and its structure was elucidated by various techniques. As an organocatalyst, its effect on enantiomeric excess (e.e.) was investigated in Michael addition studies and the best enantiomeric excess value was found to be 65% in carbontetra chloride (CCl4).

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3

Naghiyev, F. N. "THE INVESTIGATION OF MICHAEL ADDITION OF ACETOACETANILIDE AND METHYL ACETOPYRUVATE TO SOME YLIDENECYANOACETAMIDES." Azerbaijan Chemical Journal, no. 2 (June 20, 2019): 35–39. http://dx.doi.org/10.32737/0005-2531-2019-2-35-39.

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4

Bansal, Shobha, and Prabal Pratap Singh. "An Efficient Solvent Free Microwave Assisted MgFe2O4 Magnetic Nanoparticles Catalyzed Green Protocol Towards Michael Addition." Chemistry & Chemical Technology 13, no. 1 (2019): 18–22. http://dx.doi.org/10.23939/chcht13.01.018.

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5

Emori, Eita, Takayoshi Arai, Hiroaki Sasai та Masakatsu Shibasaki. "A Catalytic Michael Addition of Thiols to α,β-Unsaturated Carbonyl Compounds: Asymmetric Michael Additions and Asymmetric Protonations". Journal of the American Chemical Society 120, № 16 (1998): 4043–44. http://dx.doi.org/10.1021/ja980397v.

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6

Thirumalaikumar, Muniappan. "Enantioselective Michael Addition Reactions." Organic Preparations and Procedures International 43, no. 1 (2011): 67–129. http://dx.doi.org/10.1080/00304948.2011.547102.

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7

Reuter, Carin, and Fritz Vögtle. "Rotaxanes via Michael Addition†." Organic Letters 2, no. 5 (2000): 593–95. http://dx.doi.org/10.1021/ol990350u.

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8

Thanupran, Chatchai, Chachanat Thebtaranonth, and Yodhathai Thebtaranonth. "Stereospecific triple Michael addition." Tetrahedron Letters 27, no. 20 (1986): 2295–98. http://dx.doi.org/10.1016/s0040-4039(00)84512-8.

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9

Liao, Xi-Bin, Ji-Ye Han, and Ying Li. "Michael addition of artemisitene." Tetrahedron Letters 42, no. 15 (2001): 2843–45. http://dx.doi.org/10.1016/s0040-4039(01)00310-0.

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10

Feil, Sylvia. "Wundverschluss durch Michael-Addition?" Chemie in unserer Zeit 39, no. 4 (2005): 233. http://dx.doi.org/10.1002/ciuz.200590050.

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11

Bakó, Péter, Tamás Nemcsok, Zsolt Rapi, and György Keglevich. "Enantioselective Michael Addition of Malonates to Enones." Current Organic Chemistry 24, no. 7 (2020): 746–73. http://dx.doi.org/10.2174/1385272824666200316122221.

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: Many catalysts were tested in asymmetric Michael additions in order to synthesize enantioenriched products. One of the most common reaction types among the Michael reactions is the conjugated addition of malonates to enones making it possible to investigate the structure–activity relationship of the catalysts. The most commonly used Michael acceptors are chalcone, substituted chalcones, chalcone derivatives, cyclic enones, while typical donors may be dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, di-tert-butyl and dibenzyl malonates. This review summarizes the most important enantioselective catalysts applied in these types of reactions.

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12

EMORI, E., T. ARAI, H. SASAI та M. SHIBASAKI. "ChemInform Abstract: A Catalytic Michael Addition of Thiols to α,β-Unsaturated Carbonyl Compounds: Asymmetric Michael Additions and Asymmetric Protonations." ChemInform 29, № 33 (2010): no. http://dx.doi.org/10.1002/chin.199833051.

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13

Reznikov, Alexander N., and Yuri N. Klimochkin. "Recent Developments in Highly Stereoselective Michael Addition Reactions Catalyzed by Metal Complexes." Synthesis 52, no. 06 (2020): 781–95. http://dx.doi.org/10.1055/s-0039-1690044.

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Achieving high enantioselectivity and diastereoselectivity simultaneously is a rather challenging task for asymmetric catalytic synthesis. Thanks to the rapid development of asymmetric transition-metal catalysis, significant progress has been made during recent years in achieving highly enantio- and diastereoselective conjugate addition reactions with a diverse combination of Michael donors and acceptors. This short review surveys the advances in transition-metal-catalyzed asymmetric diastereoselective Michael addition including diastereodivergent catalysis developed between 2015 and 2019. The review is divided into multiple parts according to the type of nucleophiles involved in the reaction.1 Introduction2 Addition of Functionalized Ketones and Dicarbonyl Compounds3 Addition of Aldimino Esters and Their Cyclic Analogues4 Addition of Indolin-2-ones5 Vinylogous Michael Reactions6 Other Michael Donors7 Cascade Reactions Initiated by Michael Addition8 Conclusion

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14

Yao, Yongqi, Yingying Liu, Ling Ye, et al. "Double Michael addition of nitromethane to divinyl ketones: A remarkably positive effect of additive." Tetrahedron 73, no. 16 (2017): 2311–15. http://dx.doi.org/10.1016/j.tet.2017.03.018.

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15

Jha, S. C., and N. N. Joshi. "Catalytic, enatioselective Michael addition reactions." Arkivoc 2002, no. 7 (2002): 167–96. http://dx.doi.org/10.3998/ark.5550190.0003.718.

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16

Alexakis, A., and K. Li. "Enantioselective Michael Addition-Cyclization Reaction." Synfacts 2007, no. 7 (2007): 0738. http://dx.doi.org/10.1055/s-2007-968672.

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17

Trumbo, David L. "Michael addition polymers from bisacetoacetates." Polymer Bulletin 26, no. 5 (1991): 481–85. http://dx.doi.org/10.1007/bf01032670.

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18

Hutchinson, David W., and David M. Thornton. "Michael addition reactions of ethenylidenebisphosphonates." Journal of Organometallic Chemistry 346, no. 3 (1988): 341–48. http://dx.doi.org/10.1016/0022-328x(88)80134-7.

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19

Chen, Bi-Shuang, Verena Resch, Linda G. Otten, and Ulf Hanefeld. "Enantioselective Michael Addition of Water." Chemistry - A European Journal 21, no. 7 (2014): 3020–30. http://dx.doi.org/10.1002/chem.201405579.

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20

Enders, Dieter, Ayhan S. Demir, and Beatrice E. M. Rendenbach. "Asymmetric Michael Additions via SAMP-/RAMP-Hydrazones Enantioselective 1,4-Addition of Methyl Ketones to Knoevenagel Acceptors1)." Chemische Berichte 120, no. 10 (1987): 1731–35. http://dx.doi.org/10.1002/cber.19871201019.

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21

Enders, Dieter, Karsten Lüttgen, and Arun Narine. "Asymmetric Sulfa-Michael Additions." Synthesis 2007, no. 7 (2007): 959–80. http://dx.doi.org/10.1055/s-2007-965968.

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22

Melchiorre, P., G. Bencivenni, P. Galzerano, A. Mazzanti, and G. Bartoli. "Organocatalytic Vinylogous Michael Additions." Synfacts 2010, no. 11 (2010): 1299. http://dx.doi.org/10.1055/s-0030-1258785.

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23

Lee, Hee, Bong Kim, Aeri Park, Ji An, Won Lee, and Hyunik Shin. "Highly Improved Copper-Mediated Michael Addition of Ethyl Bromodifluoroacetate in the Presence of Protic Additive." Synthesis 44, no. 20 (2012): 3165–70. http://dx.doi.org/10.1055/s-0032-1317134.

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24

Kumar, Akshay, and Swapandeep Singh Chimni. "Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives." Beilstein Journal of Organic Chemistry 10 (April 24, 2014): 929–35. http://dx.doi.org/10.3762/bjoc.10.91.

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Simple primary-tertiary diamines easily derived from natural primary amino acids were used to catalyze the Michael addition of ketones with isatylidenemalononitrile derivatives. Diamine 1a in combination with D-CSA as an additive provided Michael adducts in high yield (up to 94%) and excellent enantioselectivity (up to 99%). The catalyst 1a was successfully used to catalyze the three-component version of the reaction by a domino Knoevenagel–Michael sequence. The Michael adduct 4a was transformed into spirooxindole 6 by a reduction with sodium borohydride in a highly enantioselective manner.

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25

Gliese, Jan-Philipp, Stefan H. Jungbauer, and Stefan M. Huber. "A halogen-bonding-catalyzed Michael addition reaction." Chemical Communications 53, no. 88 (2017): 12052–55. http://dx.doi.org/10.1039/c7cc07175b.

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26

Piers, Edward, Ernest J. McEachern, and Patricia A. Burns. "Intramolecular Michael Additions: Copper(I) Chloride-Mediated Conjugate Addition of Vinyltrimethylstannane Functions to .alpha.,.beta.-Unsaturated Ketones." Journal of Organic Chemistry 60, no. 8 (1995): 2322–23. http://dx.doi.org/10.1021/jo00113a006.

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27

Tang, Y., Q. G. Wang, X. M. Deng, et al. "Domino Asymmetric Michael Addition/Ylide Epoxidation." Synfacts 2008, no. 7 (2008): 0711. http://dx.doi.org/10.1055/s-2008-1078455.

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28

Tsuboi, Sadao, Hiroyuki Nagae, Hirofumi Yamato, and Akira Takeda. "A Michael Addition-Induced Favorskii Rearrangement." Bulletin of the Chemical Society of Japan 60, no. 2 (1987): 836–38. http://dx.doi.org/10.1246/bcsj.60.836.

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29

Mukaiyama, T., T. Tozawa, H. Nagao, and Y. Yamane. "Asymmetric Domino Mukaiyama-Michael-Addition-Lactonization." Synfacts 2007, no. 3 (2007): 0318. http://dx.doi.org/10.1055/s-2007-968233.

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30

Deng, L., and X. Lu. "Broad Scope Organocatalytic Aza-Michael Addition." Synfacts 2008, no. 11 (2008): 1222. http://dx.doi.org/10.1055/s-0028-1083385.

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31

Pansare, S., and K. Pandya. "Amine/Protonic Acid Catalyzed Michael Addition." Synfacts 2006, no. 9 (2006): 0955. http://dx.doi.org/10.1055/s-2006-949231.

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32

Błażewska, Katarzyna, Joanna Gmach, and Łukasz Joachimiak. "Aza-Michael Addition of Imidazole Analogues." Synthesis 48, no. 17 (2016): 2681–704. http://dx.doi.org/10.1055/s-0035-1560451.

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33

Vieth, Siegfried, Burkhard Costisella, and Matthias Schneider. "Tandem Michael addition alkylation of vinylphosphonates." Tetrahedron 53, no. 28 (1997): 9623–28. http://dx.doi.org/10.1016/s0040-4020(97)00648-0.

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34

Li, Hao, Liansuo Zu, Hexin Xie, Jian Wang, Wei Jiang, and Wei Wang. "Enantioselective Organocatalytic Double Michael Addition Reactions." Organic Letters 9, no. 9 (2007): 1833–35. http://dx.doi.org/10.1021/ol070581y.

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35

Reddy, S. Madhava, and H. M. Walborsky. "A facile intramolecular Michael addition reaction." Journal of Organic Chemistry 51, no. 13 (1986): 2605–7. http://dx.doi.org/10.1021/jo00363a042.

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36

Wang, X., R. T. Li, X. Ai, J. M. Liu, Z. M. Ge, and T. M. Cheng. "Aza-Michael Addition in Alkaline Al2O3." Synfacts 2010, no. 09 (2010): 1089. http://dx.doi.org/10.1055/s-0030-1257984.

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37

You, S. L., Q. Cai, and C. Zheng. "Intramolecular Aza-Michael Addition of Indoles." Synfacts 2010, no. 12 (2010): 1428. http://dx.doi.org/10.1055/s-0030-1258922.

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38

Müh, Ekkehard, Hans Weickmann, Joachim E. Klee, Holger Frey, and Rolf Mülhaupt. "Acrylate-Terminated Macromonomers by Michael Addition." Macromolecular Chemistry and Physics 202, no. 18 (2001): 3484–89. http://dx.doi.org/10.1002/1521-3935(20011201)202:18<3484::aid-macp3484>3.0.co;2-l.

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39

Wang, Tai-chi, Yeh-Long Chen, Kuan-Han Lee, and Cherng-Chyi Tzeng. "An intermolecular Michael addition of benzene." Tetrahedron Letters 37, no. 35 (1996): 6369–70. http://dx.doi.org/10.1016/0040-4039(96)01364-0.

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40

Hamlin, Trevor A., Israel Fernández, and F. Matthias Bickelhaupt. "How Dihalogens Catalyze Michael Addition Reactions." Angewandte Chemie International Edition 58, no. 26 (2019): 8922–26. http://dx.doi.org/10.1002/anie.201903196.

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41

Thirumalaikumar, Muniappan. "ChemInform Abstract: Enantioselective Michael Addition Reactions." ChemInform 42, no. 31 (2011): no. http://dx.doi.org/10.1002/chin.201131260.

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42

Yang, Hongjun, YongKang Zuo, Jiadong Zhang, et al. "Phosphazene-catalyzed oxa-Michael addition click polymerization." Polymer Chemistry 9, no. 38 (2018): 4716–23. http://dx.doi.org/10.1039/c8py01089g.

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43

Katritzky, Alan R., and Ming Qi. "Michael Additions of Benzotriazole-Stabilized Carbanions. A Review." Collection of Czechoslovak Chemical Communications 63, no. 5 (1998): 599–613. http://dx.doi.org/10.1135/cccc19980599.

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The 1,4-addition of benzotriazole-stabilized carbanions to Michael acceptors is reviewed. The selectivity between 1,4- and 1,2-addition depends significantly on the electronic effect of the carbanion (usually lithium is the counterion), the type of the Michael acceptor, and steric effects. Steric hindrance of the benzotriazolyl group probably enhances the regioselectivity. Normally, 1,4-additions to α,β-unsaturated ketone or ester are observed for carbanions stabilized by a benzotriazolyl group and an electron-withdrawing group (e.g. aryl, vinyl, carbonyl). For α,β-unsaturated aldehydes as Michael acceptors, 1,2-addition is more likely, except where electronic effects are very strong. A review with 39 references.

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44

Naganaboina, Ram Tilak, Amrita Nayak, and Rama Krishna Peddinti. "Trifluoroacetic acid-promoted Michael addition–cyclization reactions of vinylogous carbamates." Org. Biomol. Chem. 12, no. 21 (2014): 3366–70. http://dx.doi.org/10.1039/c4ob00437j.

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A simple and efficient methodology has been developed for the synthesis of pyrrolobenzoxazine and 3-arylamino coumarin derivatives promoted by trifluoroacetic acid. The initial step in the current protocol involves a Michael addition of the 1,4-benzoxazinone derivatives to the Michael acceptors and subsequent cyclization.

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45

Gandi, Vasudeva Rao, and Yixin Lu. "Phosphine-catalyzed regioselective Michael addition to allenoates." Chemical Communications 51, no. 90 (2015): 16188–90. http://dx.doi.org/10.1039/c5cc06197k.

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46

Silm, Estelle, Ivar Järving, and Tõnis Kanger. "Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole." Beilstein Journal of Organic Chemistry 18 (February 3, 2022): 167–73. http://dx.doi.org/10.3762/bjoc.18.18.

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An asymmetric Michael reaction between cyclopentane-1,2-dione and alkylidene oxindole was studied in the presence of a multifunctional squaramide catalyst. Michael adducts were obtained in high enantioselectivities and in moderate diastereoselectivities.

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47

Miyanaga, Akimasa. "Michael additions in polyketide biosynthesis." Natural Product Reports 36, no. 3 (2019): 531–47. http://dx.doi.org/10.1039/c8np00071a.

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48

Chen, Ying-Chun, Chang-Jiang Xu, Wei Du, and Łukasz Albrecht. "Lewis Basic Amine Catalyzed Aza-Michael Reaction of Indole- and Pyrrole-3-carbaldehydes." Synthesis 52, no. 18 (2020): 2650–61. http://dx.doi.org/10.1055/s-0040-1707176.

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3-Formyl substituted indoles or pyrroles can form HOMO-raised dearomative aza-dienamine-type intermediates with secondary amines, which can undergo direct aza-Michael addition to β-trifluoromethyl enones to afford N-alkylated products efficiently, albeit with low to fair enantioselectivity. In addition, similar asymmetric aza-Michael additions of these heteroarenes and crotonaldehyde are realized under dual catalysis of chiral amines, and the adducts are obtained with moderate to good enantioselectivity.

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49

Yu, Mirim, and Sung-Gon Kim. "Asymmetric organocatalytic Michael addition/aza-cyclization coupled with sequential Michael addition for synthesizing densely polycyclic-fused dihydroquinolines." Tetrahedron Letters 56, no. 28 (2015): 4159–62. http://dx.doi.org/10.1016/j.tetlet.2015.04.112.

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50

Zou, Chuncheng, Yanting Lv, Min Lu, et al. "Regioselective and diastereodivergent organocatalytic asymmetric vinylogous Michael addition." Organic Chemistry Frontiers 8, no. 17 (2021): 4758–66. http://dx.doi.org/10.1039/d1qo00371b.

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