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1

Cai, Quan, Xu-Ge Si, and Zhi-Mao Zhang. "Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis." Synlett 32, no. 10 (2021): 947–54. http://dx.doi.org/10.1055/a-1371-4391.

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AbstractDiels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.1 Introduction2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Ac
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2

Heller, Douglas P., Daniel R. Goldberg, Hongqiao Wu, and William D. Wulff. "An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions." Canadian Journal of Chemistry 84, no. 10 (2006): 1487–503. http://dx.doi.org/10.1139/v06-124.

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Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6- and 6′-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4- and 4′-positions. The set of four new ligands that have been prepared have the following groups introduced into the 6- and 6′-positions of VAPOL: bromide, methyl, phenyl and 3,5-d
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3

Kagan, Henri B., and Olivier Riant. "Catalytic asymmetric Diels Alder reactions." Chemical Reviews 92, no. 5 (1992): 1007–19. http://dx.doi.org/10.1021/cr00013a013.

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4

Kong, Liman, Xiaoyu Han, and Peng Jiao. "Catalytic asymmetric Diels–Alder reactions involving aryl vinyl ketones." Chem. Commun. 50, no. 91 (2014): 14113–16. http://dx.doi.org/10.1039/c4cc06837h.

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5

Bădoiu, Andrei, Yasmin Brinkmann, Florian Viton, and E. Peter Kündig. "Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions." Pure and Applied Chemistry 80, no. 5 (2008): 1013–18. http://dx.doi.org/10.1351/pac200880051013.

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Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate α,β-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.
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6

Fochi, Mariafrancesca, Luca Bernardi, and Lorenzo Caruana. "Catalytic Asymmetric Aza-Diels–Alder Reactions: The Povarov Cycloaddition Reaction." Synthesis 46, no. 02 (2013): 135–57. http://dx.doi.org/10.1055/s-0033-1338581.

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7

Lautens, Mark, Julia Craig Lautens, and A. Catherine Smith. "Catalytic asymmetric induction in the homo Diels-Alder reaction." Journal of the American Chemical Society 112, no. 14 (1990): 5627–28. http://dx.doi.org/10.1021/ja00170a030.

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8

Yamamoto, Yuhei, and Hisashi Yamamoto. "Catalytic Asymmetric Nitroso-Diels-Alder Reaction with Acyclic Dienes." Angewandte Chemie International Edition 44, no. 43 (2005): 7082–85. http://dx.doi.org/10.1002/anie.200501345.

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9

Yamamoto, Yuhei, and Hisashi Yamamoto. "Catalytic Asymmetric Nitroso-Diels-Alder Reaction with Acyclic Dienes." Angewandte Chemie 117, no. 43 (2005): 7244–47. http://dx.doi.org/10.1002/ange.200501345.

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10

Nakano, Hiroto, Yuichiro Suzuki, Chizuko Kabuto, Reiko Fujita, and Hiroshi Hongo. "Chiral Phosphinooxathiane Ligands for Catalytic Asymmetric Diels−Alder Reaction." Journal of Organic Chemistry 67, no. 14 (2002): 5011–14. http://dx.doi.org/10.1021/jo0201474.

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11

KAGAN, H. B., and O. RIANT. "ChemInform Abstract: Catalytic Asymmetric Diels-Alder Reactions." ChemInform 23, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199245318.

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12

Wei, Liang, Qiao Zhu, Zhi-Min Song, Kang Liu, and Chun-Jiang Wang. "Catalytic asymmetric inverse electron demand Diels–Alder reaction of fulvenes with azoalkenes." Chemical Communications 54, no. 20 (2018): 2506–9. http://dx.doi.org/10.1039/c7cc09896k.

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An unprecedented copper(i)-catalyzed asymmetric inverse electron demand Diels–Alder reaction of azoalkenes with fulvenes is reported. This methodology offers a directed entry to synthesize bicyclic tetrapyridazine derivatives in good yield with exclusive regioselectivity and excellent stereoselectivity.
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13

Gong, Liu-Zhu, Nan Li, Dian-Feng Chen, Pu-Sheng Wang, and Zhi-Yong Han. "Relay Catalytic Cascade Hydrosiloxylation and Asymmetric Hetero-Diels–Alder Reaction." Synthesis 46, no. 10 (2014): 1355–61. http://dx.doi.org/10.1055/s-0033-1340905.

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14

Ullah, Md Wali, and Naoki Haraguchi. "Ionic, Core-Corona Polymer Microsphere-Immobilized MacMillan Catalyst for Asymmetric Diels-Alder Reaction." Catalysts 9, no. 11 (2019): 960. http://dx.doi.org/10.3390/catal9110960.

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The improvement of the catalytic activity of a heterogeneous chiral catalyst is one of the most critical issues, as are its recovery and reuse. The design of a heterogeneous chiral catalyst, including the immobilization method and the support polymer, is of significance for the catalytic activity in asymmetric reactions. An ionic, core-corona polymer microsphere-immobilized MacMillan catalyst (ICCC) was successfully synthesized by the neutralization reaction of sulfonic acid functionalized core-corona polymer microsphere (CCM–SO3H) with a chiral imidazolidinone precursor. We selected the core-
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15

Fochi, Mariafrancesca, Lorenzo Caruana, and Luca Bernardi. "ChemInform Abstract: Catalytic Asymmetric Aza-Diels-Alder Reactions: The Povarov Cycloaddition Reaction." ChemInform 45, no. 15 (2014): no. http://dx.doi.org/10.1002/chin.201415264.

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16

Silva, Eduarda, Artur Silva, and Djenisa Rocha. "Diels–Alder Reactions of 1,2-Dihydropyridines: An Efficient Tool for the Synthesis of Isoquinuclidines." Synthesis 50, no. 09 (2018): 1773–82. http://dx.doi.org/10.1055/s-0037-1609418.

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The Diels–Alder reaction of 1,2-dihydropyridines with different dienophiles is a well-established and straightforward method for the synthesis of isoquinuclidines. Nevertheless, the enantioselective preparation of isoquinuclidines using organocatalysts or organometallic catalysts is rather unexplored. This succinct review offers readers an overall perspective of the most important recent developments and concepts related to this topic.1 Introduction2 Asymmetric Diels–Alder Reaction of 1,2-Dihydropyridines2.1 Transition-Metal-Catalyzed Reactions2.2 Organocatalyzed Reactions3 Diels–Alder Reactio
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17

Yamashita, Yasuhiro, and Shu Kobayashi. "ChemInform Abstract: Catalytic Asymmetric Aza Diels-Alder Reactions." ChemInform 41, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.201031263.

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18

Bueno, Maria P., Carlos Cativiela, José A. Mayoral, et al. "Natural amino acids as chiral auxiliaries in asymmetric Diels–Alder reactions." Canadian Journal of Chemistry 66, no. 11 (1988): 2826–29. http://dx.doi.org/10.1139/v88-437.

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To test whether α-amino acids can be efficient chiral auxiliaries in asymmetric Diels–Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene. Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1R,2R)-cycloadduct were achieved with AlCl3, the reaction did not show diastereofacial selectivity when titanium catalysts were used. Moreover, with Ti(iPrO)4 a transesterification reaction, which leads to the isopropyl ester and competes with the Diels–
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19

Zhang, Dongxin, and Fujie Tanaka. "Catalytic enantioselective oxa-hetero-Diels–Alder reactions of enones with aryl trifluoromethyl ketones." RSC Advances 6, no. 66 (2016): 61454–57. http://dx.doi.org/10.1039/c6ra13859d.

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Asymmetric oxa-hetero-Diels–Alder reactions of enones with aryl trifluoromethyl ketones were developed to afford tetrahydropyranones bearing trifluoromethyl-substituted tetrasubstituted carbon centers.
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20

Jiang, Xianxing, and Rui Wang. "Recent Developments in Catalytic Asymmetric Inverse-Electron-Demand Diels–Alder Reaction." Chemical Reviews 113, no. 7 (2013): 5515–46. http://dx.doi.org/10.1021/cr300436a.

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21

Nakano, Hiroto, Yuichiro Suzuki, Chizuko Kabuto, Reiko Fujita, and Hiroshi Hongo. "ChemInform Abstract: Chiral Phosphinooxathiane Ligands for Catalytic Asymmetric Diels-Alder Reaction." ChemInform 33, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.200246031.

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22

Zhao, Qun, Yao Li, Qing‐Xia Zhang, Jin‐Pei Cheng, and Xin Li. "Catalytic Asymmetric Aza‐Diels–Alder Reaction of Ketimines and Unactivated Dienes." Angewandte Chemie 133, no. 32 (2021): 17749–55. http://dx.doi.org/10.1002/ange.202104788.

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23

Zhao, Qun, Yao Li, Qing‐Xia Zhang, Jin‐Pei Cheng, and Xin Li. "Catalytic Asymmetric Aza‐Diels–Alder Reaction of Ketimines and Unactivated Dienes." Angewandte Chemie International Edition 60, no. 32 (2021): 17608–14. http://dx.doi.org/10.1002/anie.202104788.

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24

Du, Haifeng, and Kuiling Ding. "ChemInform Abstract: Asymmetric Catalysis of Diels-Alder Reaction." ChemInform 41, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.201031264.

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25

Balskus, E. P., and E. N. Jacobsen. "Asymmetric Catalysis of the Transannular Diels-Alder Reaction." Science 317, no. 5845 (2007): 1736–40. http://dx.doi.org/10.1126/science.1146939.

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26

Cole, Charles J. F., Lilia Fuentes, and Scott A. Snyder. "Asymmetric pyrone Diels–Alder reactions enabled by dienamine catalysis." Chemical Science 11, no. 8 (2020): 2175–80. http://dx.doi.org/10.1039/c9sc05738b.

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A dienamine mediated asymmetric Diels–Alder reaction between an array of α,β-unsaturated enals and electron-deficient pyrones is presented along with further transformations of the obtained products and models for the observed stereoselectivity.
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27

Zagidullin, A. A., E. S. Oshchepkova, I. V. Chuchelkin, et al. "P-Chiral 1,7-diphosphanorbornenes: from asymmetric phospha-Diels–Alder reactions towards applications in asymmetric catalysis." Dalton Transactions 48, no. 14 (2019): 4677–84. http://dx.doi.org/10.1039/c9dt00443b.

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28

Markó, István E., Graham R. Evans, and Jean-Paul Declercq. "Catalytic asymmetric Diels-Alder reactions of 2-pyrone derivatives." Tetrahedron 50, no. 15 (1994): 4557–74. http://dx.doi.org/10.1016/s0040-4020(01)89387-x.

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29

Xie, Mingsheng, Lili Lin, and Xiaoming Feng. "Catalytic Asymmetric Inverse‐Electron‐Demand Hetero‐Diels−Alder Reactions." Chemical Record 17, no. 12 (2017): 1184–202. http://dx.doi.org/10.1002/tcr.201700006.

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30

Liang, Tao, Guilong Li, Lukasz Wojtas, and Jon C. Antilla. "Chiral metal phosphate catalysis: highly asymmetric hetero-Diels–Alder reactions." Chem. Commun. 50, no. 91 (2014): 14187–90. http://dx.doi.org/10.1039/c4cc06520d.

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31

Zhou, You-Yun, and Christopher Uyeda. "Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes." Science 363, no. 6429 (2019): 857–62. http://dx.doi.org/10.1126/science.aau0364.

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Cycloaddition reactions provide direct and convergent routes to cycloalkanes, making them valuable targets for the development of synthetic methods. Whereas six-membered rings are readily accessible from Diels-Alder reactions, cycloadditions that generate five-membered rings are comparatively limited in scope. Here, we report that dinickel complexes catalyze [4 + 1]-cycloaddition reactions of 1,3-dienes. The C1partner is a vinylidene equivalent generated from the reductive activation of a 1,1-dichloroalkene in the presence of stoichiometric zinc. Intermolecular and intramolecular variants of t
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32

Su, Zhishan, and Chan Kyung Kim. "Trienamine catalysis for asymmetric Diels–Alder reactions of 2,4-dienones: a theoretical investigation." Organic & Biomolecular Chemistry 13, no. 22 (2015): 6313–24. http://dx.doi.org/10.1039/c5ob00797f.

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In the Diels–Alder reactions of 2,4-dienones with two dienophiles, cinchona alkaloid acts as an efficient bifunctional catalyst by generating an extended trienamine π-conjugated system and by orienting the dienophile at an appropriate position for a cycloaddition reaction.
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33

Lee, Woong-Sup, Linzi Li, and Byeong Moon Kim. "SuFEx-Click Approach for the Synthesis of Soluble Polymer-Bound MacMillan Catalysts for the Asymmetric Diels–Alder Reaction." Catalysts 11, no. 9 (2021): 1044. http://dx.doi.org/10.3390/catal11091044.

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Novel polymeric MacMillan catalysts were prepared from modified chiral imidazolidin-4-one monomers via sulfur(VI) fluoride exchange chemistry. The resulting polysulfates containing chiral imidazolidin-4-one units could be employed as polymeric organocatalysts for the asymmetric Diels–Alder reaction. With the use of these polysulfate catalysts, sufficient catalytic activity and enantioselectivity were obtained, which were similar to those obtained by monomeric catalysts in a homogeneous catalytic reaction. In addition, the polysulfate catalysts could be recovered and reused five times without a
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34

Yao, Sulan, Mogens Johannsen, Hélène Audrain, Rita G. Hazell, and Karl Anker Jørgensen. "Catalytic Asymmetric Hetero-Diels−Alder Reactions of Ketones: Chemzymatic Reactions." Journal of the American Chemical Society 120, no. 34 (1998): 8599–605. http://dx.doi.org/10.1021/ja981710w.

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35

Pineschi, Mauro, Federica Del Moro, Paolo Crotti, and Franco Macchia. "Catalytic asymmetric ring-opening of cyclopentadiene - heterodienophile cycloadducts with organometallic reagents." Pure and Applied Chemistry 78, no. 2 (2006): 463–67. http://dx.doi.org/10.1351/pac200678020463.

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An unprecedented catalytic asymmetric ring-opening of easily accessible 2,3-heterosubstituted norbornenes with hard alkyl metals (R-M), is able to give a practical regio- and stereoselective access to hetero-functionalized alkyl cyclopentenes in an enantioenriched form. The copper-catalyzed desymmetrization reaction with trialkylaluminums of sterically hindered and rigid, tri- or tetracyclic Diels-Alder adducts, easily available by cycloaddition reaction of cyclopentadiene with 4-phenyl-urazole and 2,3-phthalazine-1,4-dione, proved to be particularly efficient. Interestingly, the chirality of
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36

Reid, Jolene P., Mingyou Hu, Susumu Ito та ін. "Strategies for remote enantiocontrol in chiral gold(iii) complexes applied to catalytic enantioselective γ,δ-Diels–Alder reactions". Chemical Science 11, № 25 (2020): 6450–56. http://dx.doi.org/10.1039/d0sc00497a.

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Chiral square planar gold(iii) complexes are employed as catalysts in asymmetric Diels–Alder reactions. The non-covalent interactions responsible for the enantioselectivity are revealed through multivariate linear regression analysis.
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37

Bulman Page, Philip C., Francesca S. Kinsey, Yohan Chan, Ian R. Strutt, Alexandra M. Z. Slawin та Garth A. Jones. "Novel binaphthyl and biphenyl α- and β-amino acids and esters: organocatalysis of asymmetric Diels–Alder reactions. A combined synthetic and computational study". Organic & Biomolecular Chemistry 16, № 40 (2018): 7400–7416. http://dx.doi.org/10.1039/c8ob01795f.

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Asymmetric catalysis of the Diels–Alder reaction between cyclopentadiene and cinnamaldehydes has been studied using as catalysts a range of novel α- and β-aminoacids and aminoesters with binaphthyl and biphenyl backbones.
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38

Zhou, Yuhang, Lili Lin, Xiaohua Liu, et al. "Catalytic Asymmetric Diels-Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1-Thiocyanatobutadienes." Angewandte Chemie 130, no. 29 (2018): 9251–54. http://dx.doi.org/10.1002/ange.201804811.

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39

Li, Nan, Dian-Feng Chen, Pu-Sheng Wang, Zhi-Yong Han, and Liu-Zhu Gong. "ChemInform Abstract: Relay Catalytic Cascade Hydrosiloxylation and Asymmetric Hetero-Diels-Alder Reaction." ChemInform 45, no. 44 (2014): no. http://dx.doi.org/10.1002/chin.201444192.

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40

Zhou, Yuhang, Lili Lin, Xiaohua Liu, et al. "Catalytic Asymmetric Diels-Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1-Thiocyanatobutadienes." Angewandte Chemie International Edition 57, no. 29 (2018): 9113–16. http://dx.doi.org/10.1002/anie.201804811.

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41

Narine, Arun A., and Peter D. Wilson. "Synthesis and evaluation of 7-hydroxyindan-1-one-derived chiral auxiliaries." Canadian Journal of Chemistry 83, no. 5 (2005): 413–19. http://dx.doi.org/10.1139/v05-052.

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A series of novel chiral acetals were prepared from 7-hydroxyindan-1-one and a variety of substituted chiral nonracemic C2-symmetric 1,2-ethanediols (R = Me, Ph, CH2OMe, CH2OBn, CH2O(1-Np), and i-Pr). These acetals were evaluated as chiral auxiliaries for use in asymmetric synthesis. A high degree of stereochemical induction was observed in the diethylaluminum chloride-promoted Diels–Alder reaction of an acrylate derivative (R = i-Pr) with cyclopentadiene (91:9 dr). This demonstrated that these acetals could serve as effective chiral directors in asymmetric substrate-directed reactions.Key wor
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42

Uemura, Naohiro, Seiya Toyoda, Waku Shimizu, Yasushi Yoshida, Takashi Mino, and Masami Sakamoto. "Absolute Asymmetric Synthesis Involving Chiral Symmetry Breaking in Diels–Alder Reaction." Symmetry 12, no. 6 (2020): 910. http://dx.doi.org/10.3390/sym12060910.

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Efficient generation and amplification of chirality from prochiral substrates in the Diels–Alder reaction (DA reaction) followed by dynamic crystallization were achieved without using an external chiral source. Since the DA reaction of 2-methylfuran and various maleimides proceeds reversibly, an exo-adduct was obtained as the main product as the reaction proceeded. From single crystal X-ray structure analysis, it was found that five of ten exo-adducts gave conglomerates. When 2-methylfuran and various maleimides with a catalytic amount of TFA were reacted in a sealed tube, the exo-DA adducts w
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43

Bakhtiari, Atefeh, and Javad Safaei-Ghomi. "Effects of Chiral Ligands on the Asymmetric Carbonyl-Ene Reaction." Synlett 30, no. 15 (2019): 1738–64. http://dx.doi.org/10.1055/s-0037-1611875.

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The carbonyl-ene reaction is one of the most well-known reactions for C–C bond formation. Based on frontier molecular orbitals (FMO), carbonyl-ene reactions occur between the highest occupied molecular orbital (HOMO) of the ene compound bearing an active hydrogen atom at the allylic center and the lowest unoccupied molecular orbital (LUMO) of the electron-deficient enophile, which is a carbonyl compound. A high activation barrier enforces the concerted ene reaction rather than a Diels–Alder reaction at high temperature. Employing a catalytic system can eliminate defects in the ene reaction, an
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44

Yeung, Chi-Tung, Wesley Ting Kwok Chan, Wai-Sum Lo, Ga-Lai Law, and Wing-Tak Wong. "Catalytic asymmetric oxo-Diels–Alder reactions with chiral atropisomeric biphenyl diols." Beilstein Journal of Organic Chemistry 15 (April 18, 2019): 955–62. http://dx.doi.org/10.3762/bjoc.15.92.

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New chiral atropisomeric biphenyl diols 3, 4 and 6 containing additional peripheral chiral centers with different steric bulkiness and/or electronic properties were synthesized. The X-ray crystal structure of 3 shows the formation of a supramolecular structure whereas that of 6, containing additional CF3 substituents, shows the formation of a monomeric structure. Diols 1–6 were found to be active organocatalysts in oxo-Diels–Alder reactions in which 2 recorded a 72% ee with trimethylacetaldehyde as a substrate.
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45

Möller, Tobias, Peter Wonneberger, Nadja Kretzschmar, and Evamarie Hey-Hawkins. "P-chiral phosphorus heterocycles: a straightforward synthesis." Chem. Commun. 50, no. 44 (2014): 5826–28. http://dx.doi.org/10.1039/c4cc00318g.

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46

Lockett-Walters, Bruce, Cristina Trujillo, Brendan Twamley, and Stephen Connon. "The base-catalysed Tamura cycloaddition reaction: calculation, mechanism, isolation of intermediates and asymmetric catalysis." Chemical Communications 55, no. 75 (2019): 11283–86. http://dx.doi.org/10.1039/c9cc05064g.

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47

Li, Yang, Casper Barløse, Julie Jørgensen, Bjørn Dreiø Carlsen, and Karl Anker Jørgensen. "Asymmetric Catalytic Aza-Diels-Alder/Ring-Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis." Chemistry - A European Journal 23, no. 1 (2016): 38–41. http://dx.doi.org/10.1002/chem.201604310.

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48

Li, Yang, Casper Barløse, Julie Jørgensen, Bjørn Dreiø Carlsen, and Karl Anker Jørgensen. "Asymmetric Catalytic Aza-Diels-Alder/Ring-Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis." Chemistry - A European Journal 23, no. 1 (2016): 3. http://dx.doi.org/10.1002/chem.201605562.

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49

Li, Tian-Ze, Chang-An Geng, Xiu-Juan Yin, et al. "Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction." Organic Letters 19, no. 3 (2017): 429–31. http://dx.doi.org/10.1021/acs.orglett.6b03801.

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50

Shibatomi, Kazutaka, Kentaro Futatsugi, Fumito Kobayashi, Seiji Iwasa, and Hisashi Yamamoto. "Stereoselective Construction of Halogenated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels−Alder Reaction." Journal of the American Chemical Society 132, no. 16 (2010): 5625–27. http://dx.doi.org/10.1021/ja1018628.

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