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Journal articles on the topic 'Enantioselective cycloisomerizations'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Marinetti, Angela, Hélène Jullien, and Arnaud Voituriez. "Enantioselective, transition metal catalyzed cycloisomerizations." Chemical Society Reviews 41, no. 14 (2012): 4884. http://dx.doi.org/10.1039/c2cs35020c.

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2

Marinetti, Angela, Helene Jullien, and Arnaud Voituriez. "ChemInform Abstract: Enantioselective, Transition Metal Catalyzed Cycloisomerizations." ChemInform 43, no. 42 (2012): no. http://dx.doi.org/10.1002/chin.201242253.

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3

Zhang, Yang, Hélène Jullien, Delphine Brissy, Pascal Retailleau, Arnaud Voituriez, and Angela Marinetti. "Platinum(II) Catalyzed Enantioselective Cycloisomerizations of 3-Hydroxylated 1,5-Enynes." ChemCatChem 5, no. 7 (2013): 2051–57. http://dx.doi.org/10.1002/cctc.201200743.

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4

Dieckmann, Michael, Yun-Suk Jang, and Nicolai Cramer. "Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes." Angewandte Chemie 127, no. 41 (2015): 12317–20. http://dx.doi.org/10.1002/ange.201506483.

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5

Dieckmann, Michael, Yun-Suk Jang, and Nicolai Cramer. "Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes." Angewandte Chemie International Edition 54, no. 41 (2015): 12149–52. http://dx.doi.org/10.1002/anie.201506483.

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6

Nguyen, Xuan B., Yuji Nakano, and David W. Lupton. "Polarity Inversion Catalysis by the 1,4-Addition of N-Heterocyclic Carbenes." Australian Journal of Chemistry 73, no. 1 (2020): 1. http://dx.doi.org/10.1071/ch19550.

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Polarity inversion is the hallmark of N-heterocyclic carbene (NHC) organocatalysis, with the generation and reaction of acyl anion equivalents known for more than 70 years. In contrast, polarity inversion through 1,4-addition of NHCs to conjugate acceptors was first applied in a catalytic reaction in 2006. This sub-field of NHC-organocatalysis has developed steadily over the subsequent years, enabling novel coupling reactions, enantioselective cycloisomerizations, polymerizations, and other reactions. In this review, this emerging area of NHC-organocatalysis is discussed with comprehensive cov

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7

Zhang, Yang, Helene Jullien, Delphine Brissy, Pascal Retailleau, Arnaud Voituriez, and Angela Marinetti. "ChemInform Abstract: Platinum(II) Catalyzed Enantioselective Cycloisomerizations of 3-Hydroxylated 1,5-Enynes." ChemInform 44, no. 46 (2013): no. http://dx.doi.org/10.1002/chin.201346041.

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8

Dieckmann, Michael, Yun-Suk Jang, and Nicolai Cramer. "ChemInform Abstract: Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes." ChemInform 47, no. 7 (2016): no. http://dx.doi.org/10.1002/chin.201607172.

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9

Trost, Barry M., Li Dong, and Gretchen M. Schroeder. "Exploiting the Pd- and Ru-Catalyzed Cycloisomerizations: Enantioselective Total Synthesis of (+)-Allocyathin B2." Journal of the American Chemical Society 127, no. 29 (2005): 10259–68. http://dx.doi.org/10.1021/ja051547m.

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10

Brissy, Delphine, Myriem Skander, Hélène Jullien, Pascal Retailleau, and Angela Marinetti. "Platinum(II) Catalysts for Highly Enantioselective 1,6-Enyne Cycloisomerizations. Synthetic, Structural, and Catalytic Studies." Organic Letters 11, no. 10 (2009): 2137–39. http://dx.doi.org/10.1021/ol900724z.

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11

Guo, Rui, Kang-Nan Li, Bin Liu, Hua-Jie Zhu, Yu-Meng Fan, and Liu-Zhu Gong. "Asymmetric synthesis of heteroaryl atropisomers via a gold-catalyzed cycloisomerization–amination cascade reaction." Chem. Commun. 50, no. 41 (2014): 5451–54. http://dx.doi.org/10.1039/c4cc01397b.

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12

Wu, Zhiyong, David Lebœuf, Pascal Retailleau, Vincent Gandon, Angela Marinetti, and Arnaud Voituriez. "Enantioselective gold(i)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes." Chemical Communications 53, no. 52 (2017): 7026–29. http://dx.doi.org/10.1039/c7cc03234j.

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A gold(i)-catalyzed cycloisomerization/ring expansion sequence allows the highly enantioselective synthesis of 2-oxocyclobutylcyclopentane derivatives from cyclopropyl-substituted enynes (up to 99% ee).

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13

Zhou, Liejin, and Lu Liu. "Highly enantioselective tandem cycloisomerization/Diels–Alder reaction of 2-(1-alkynyl)-2-alken-1-ones and enals: dual catalysis with platinum and amines." Chemical Communications 57, no. 46 (2021): 5690–93. http://dx.doi.org/10.1039/d1cc02080c.

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14

Starý, Ivo, Irena G. Stará, Zuzana Alexandrová, et al. "Helicity control in the synthesis of helicenes and related compounds." Pure and Applied Chemistry 78, no. 2 (2006): 495–99. http://dx.doi.org/10.1351/pac200678020495.

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Asymmetric synthesis of helicenes and their congeners has been demonstrated to rely either on enantioselective Ni0/PR3*-catalyzed [2+2+2] cycloisomerization of triynes or on diastereoselective CoI-catalyzed [2+2+2] cycloisomerization of chiral triynes. The former approach providing tetrahydrohelicenes in a nonracemic form requires further development as moderate enantioselectivities (up to 54 % ee) have so far been achieved under kinetic control. The latter approach affording helicene-like structures in a diastereomerically enriched form allows for reaching good to excellent diastereoselectivi

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15

Liang, Ren‐Xiao, Ling‐Jie Song, Jin‐Bo Lu, Wei‐Yan Xu, Chao Ding, and Yi‐Xia Jia. "Palladium‐Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction." Angewandte Chemie International Edition 60, no. 13 (2021): 7412–17. http://dx.doi.org/10.1002/anie.202014796.

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16

Liang, Ren‐Xiao, Ling‐Jie Song, Jin‐Bo Lu, Wei‐Yan Xu, Chao Ding, and Yi‐Xia Jia. "Palladium‐Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction." Angewandte Chemie 133, no. 13 (2021): 7488–93. http://dx.doi.org/10.1002/ange.202014796.

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17

Zhao, Ping, and Xinjun Luan. "Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction." Chinese Journal of Organic Chemistry 41, no. 6 (2021): 2520. http://dx.doi.org/10.6023/cjoc202100043.

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18

Le Boucher d’Herouville, Florent, Anthony Millet, Michelangelo Scalone, and Véronique Michelet. "Synthesis of Atropisomeric MeOBIPHEP Analogues and Their Application in Silver-Catalyzed Cycloisomerization of Allenols." Synthesis 48, no. 19 (2016): 3309–16. http://dx.doi.org/10.1055/s-0035-1562448.

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The preparation of novel MeOBIPHEP atropisomeric chiral congener ligands via an efficient palladium-catalyzed P–C coupling key step is described. We demonstrate that these palladium-catalyzed conditions are compatible with the brominated MeOBIPHEP backbone. The reaction conditions for asymmetric silver-catalyzed cycloisomerization of γ-allenols were optimized, leading to the first enantioselective catalytic system employing atropisomeric diphosphine ligands as the chiral inducer. The process follows a major 5-exo cyclization via addition of the alcohol moiety to the π-activated allenyl interme

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19

Alexandrová, Zuzana, Petr Sehnal, Irena G. Stará, et al. "Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers." Collection of Czechoslovak Chemical Communications 71, no. 8 (2006): 1256–64. http://dx.doi.org/10.1135/cccc20061256.

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A practical synthesis of racemic heptahelicene has been develeped being based on key [2+2+2] cycloisomerization of bis[2-(but-3-yn-1-yl)-1-naphthyl]acetylene under CpCo(CO)2/PPh3 or CpCo(C2H4)2 catalysis. The application of the Ni(cod)2 catalyst with (-)-(Sa)-(2'-methoxy-1,1'-binaphthalen-2-yl)diphenylphosphane resulted in enantioselective triyne cyclization to provide (+)-7,8,11,12-tetrahydroheptahelicene in 40% ee. Optically pure (-)-(M)- and optically highly enriched (+)-(P)-heptahelicene were obtained on a milligram scale by resolution of racemate by chiral HPLC on a semipreparative Whelk-

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20

Gicquiaud, Julien, Baptiste Abadie, Kalyan Dhara, et al. "Brønsted Acid‐Catalyzed Enantioselective Cycloisomerization of Arylalkynes." Chemistry – A European Journal 26, no. 69 (2020): 16266–71. http://dx.doi.org/10.1002/chem.202003783.

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21

Lei, Honghui, Shan Xin, Yifan Qiu, and Xumu Zhang. "Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(i)-catalyzed asymmetric enyne cycloisomerization." Chemical Communications 54, no. 7 (2018): 727–30. http://dx.doi.org/10.1039/c7cc07967b.

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22

Deng, Xu, Shao-Fei Ni, Zheng-Yu Han, et al. "Enantioselective Rhodium-Catalyzed Cycloisomerization of (E )-1,6-Enynes." Angewandte Chemie International Edition 55, no. 21 (2016): 6295–99. http://dx.doi.org/10.1002/anie.201601061.

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23

Deng, Xu, Shao-Fei Ni, Zheng-Yu Han, et al. "Enantioselective Rhodium-Catalyzed Cycloisomerization of (E )-1,6-Enynes." Angewandte Chemie 128, no. 21 (2016): 6403–7. http://dx.doi.org/10.1002/ange.201601061.

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24

Cao, Ping, and Xumu Zhang. "The First Highly Enantioselective Rh-Catalyzed Enyne Cycloisomerization." Angewandte Chemie 39, no. 22 (2000): 4104–6. http://dx.doi.org/10.1002/1521-3773(20001117)39:22<4104::aid-anie4104>3.0.co;2-x.

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25

Cao, Ping, and Xumu Zhang. "The First Highly Enantioselective Rh-Catalyzed Enyne Cycloisomerization." Angewandte Chemie 112, no. 22 (2000): 4270–72. http://dx.doi.org/10.1002/1521-3757(20001117)112:22<4270::aid-ange4270>3.0.co;2-8.

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26

Watson, Iain D. G., and F. Dean Toste. "Catalytic enantioselective carbon-carbon bond formation using cycloisomerization reactions." Chemical Science 3, no. 10 (2012): 2899. http://dx.doi.org/10.1039/c2sc20542d.

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27

Marinetti, Angela, and Delphine Brissy. "ChemInform Abstract: Chiral Phosphorus Ligands for Enantioselective Enyne Cycloisomerization." ChemInform 43, no. 9 (2012): no. http://dx.doi.org/10.1002/chin.201209265.

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28

Toullec, Patrick Yves, Chung-Meng Chao, Qian Chen, Serafino Gladiali, Jean-Pierre Genêt, and Véronique Michelet. "Enantioselective Platinum-Catalyzed Tandem Hydroarylation- Cycloisomerization of 1,6-Enynes." Advanced Synthesis & Catalysis 350, no. 14-15 (2008): 2401–8. http://dx.doi.org/10.1002/adsc.200800446.

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29

Cao, Ping, and Xumu Zhang. "ChemInform Abstract: The First Highly Enantioselective Rh-Catalyzed Enyne Cycloisomerization." ChemInform 32, no. 13 (2001): no. http://dx.doi.org/10.1002/chin.200113119.

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30

Park, Jung-Woo, Zhiwei Chen, and Vy M. Dong. "Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers." Journal of the American Chemical Society 138, no. 10 (2016): 3310–13. http://dx.doi.org/10.1021/jacs.6b01445.

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31

Watson, Iain D. G., and F. Dean Toste. "ChemInform Abstract: Catalytic Enantioselective Carbon-Carbon Bond Formation Using Cycloisomerization Reactions." ChemInform 43, no. 50 (2012): no. http://dx.doi.org/10.1002/chin.201250242.

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32

Goeke, Andreas, Ryoichi Kuwano, Yoshihiko Ito, and Masaya Sawamura. "Enantioselective Cycloisomerization of 1,6-Enynes Catalyzed by Chiral Diphosphane–Palladium Complexes." Angewandte Chemie International Edition in English 35, no. 6 (1996): 662–63. http://dx.doi.org/10.1002/anie.199606621.

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33

Zheng, Hongchao, Ryan J. Felix, and Michel R. Gagné. "Gold-Catalyzed Enantioselective Ring-Expanding Cycloisomerization of Cyclopropylidene Bearing 1,5-Enynes." Organic Letters 16, no. 8 (2014): 2272–75. http://dx.doi.org/10.1021/ol5007955.

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34

Watson, Iain D. G., and F. Dean Toste. "ChemInform Abstract: Catalytic Enantioselective Carbon-Carbon Bond Formation Using Cycloisomerization Reactions." ChemInform 44, no. 10 (2013): no. http://dx.doi.org/10.1002/chin.201310218.

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35

KÃ¶rber, Nadine, Frank Rominger, and Thomas J. â J. MÃ¼ller. "Novel Enantioselective Sequentially Rhodium(I)/BINAP- Catalyzed CycloisomerizationâHydrogenationâIsomerizationâ Acetalization (CIHIA)." Advanced Synthesis & Catalysis 351, no. 17 (2009): 2921–35. http://dx.doi.org/10.1002/adsc.200900494.

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36

Shibata, Takanori, Ninna Uno, Tomoya Sasaki, and Kyalo Stephen Kanyiva. "Pt-Catalyzed Enantioselective Cycloisomerization for the Synthesis of Planar-Chiral Ferrocene Derivatives." Journal of Organic Chemistry 81, no. 15 (2016): 6266–72. http://dx.doi.org/10.1021/acs.joc.6b00825.

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37

Feducia, Jeremy A., Alison N. Campbell, Michael Q. Doherty, and Michel R. Gagné. "Modular Catalysts for Diene Cycloisomerization: Rapid and Enantioselective Variants for Bicyclopropane Synthesis." Journal of the American Chemical Society 128, no. 40 (2006): 13290–97. http://dx.doi.org/10.1021/ja064335d.

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38

Manzano, Rubén, Swarup Datta, Robert S. Paton, and Darren J. Dixon. "Enantioselective Silver and Amine Co-catalyzed Desymmetrizing Cycloisomerization of Alkyne-Linked Cyclohexanones." Angewandte Chemie 129, no. 21 (2017): 5928–32. http://dx.doi.org/10.1002/ange.201612048.

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39

Jullien, Hélène, Delphine Brissy, Pascal Retailleau, and Angela Marinetti. "Enantioselective Cycloisomerization of 1,5-Enynes Promoted by Cyclometalated NHC-PtII-Monophos Catalysts." European Journal of Inorganic Chemistry 2011, no. 33 (2011): 5083–86. http://dx.doi.org/10.1002/ejic.201100818.

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40

Manzano, Rubén, Swarup Datta, Robert S. Paton, and Darren J. Dixon. "Enantioselective Silver and Amine Co-catalyzed Desymmetrizing Cycloisomerization of Alkyne-Linked Cyclohexanones." Angewandte Chemie International Edition 56, no. 21 (2017): 5834–38. http://dx.doi.org/10.1002/anie.201612048.

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41

Ito, Mamoru, Moeka Okamura, Kyalo Stephen Kanyiva, and Takanori Shibata. "Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization." Organometallics 38, no. 20 (2019): 4029–35. http://dx.doi.org/10.1021/acs.organomet.9b00422.

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42

Imase, Hidetomo, Takeshi Suda, Yu Shibata, Keiichi Noguchi, Masao Hirano, and Ken Tanaka. "Highly Enantioselective Construction of Axial Chirality by Palladium-Catalyzed Cycloisomerization ofN-Alkenyl Arylethynylamides." Organic Letters 11, no. 8 (2009): 1805–8. http://dx.doi.org/10.1021/ol900373z.

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43

Huang, Long, Hai-Bin Yang, Di-Han Zhang, et al. "Gold-Catalyzed Intramolecular Regio- and Enantioselective Cycloisomerization of 1,1-Bis(indolyl)-5-alkynes." Angewandte Chemie International Edition 52, no. 26 (2013): 6767–71. http://dx.doi.org/10.1002/anie.201302632.

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44

Zheng, Hongchao, Ryan J. Felix, and Michel R. Gagne. "ChemInform Abstract: Gold-Catalyzed Enantioselective Ring-Expanding Cycloisomerization of Cyclopropylidene Bearing 1,5-Enynes." ChemInform 45, no. 40 (2014): no. http://dx.doi.org/10.1002/chin.201440062.

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45

Zhou, Liejin, Xingxing Wu, Xing Yang, et al. "Gold and Carbene Relay Catalytic Enantioselective Cycloisomerization/Cyclization Reactions of Ynamides and Enals." Angewandte Chemie International Edition 59, no. 4 (2019): 1557–61. http://dx.doi.org/10.1002/anie.201910922.

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46

Huang, Long, Hai-Bin Yang, Di-Han Zhang, et al. "Gold-Catalyzed Intramolecular Regio- and Enantioselective Cycloisomerization of 1,1-Bis(indolyl)-5-alkynes." Angewandte Chemie 125, no. 26 (2013): 6899–903. http://dx.doi.org/10.1002/ange.201302632.

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47

Zhou, Liejin, Xingxing Wu, Xing Yang, et al. "Gold and Carbene Relay Catalytic Enantioselective Cycloisomerization/Cyclization Reactions of Ynamides and Enals." Angewandte Chemie 132, no. 4 (2019): 1573–77. http://dx.doi.org/10.1002/ange.201910922.

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48

Shibata, Takanori, Yuka Kobayashi, Shunsuke Maekawa, Natsuko Toshida, and Kentaro Takagi. "Iridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes." Tetrahedron 61, no. 38 (2005): 9018–24. http://dx.doi.org/10.1016/j.tet.2005.07.039.

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49

Lei, Aiwen, Jason P. Waldkirch, Minsheng He, and Xumu Zhang. "Highly Enantioselective Cycloisomerization of Enynes Catalyzed by Rhodium for the Preparation of Functionalized Lactams." Angewandte Chemie International Edition 41, no. 23 (2002): 4526–29. http://dx.doi.org/10.1002/1521-3773(20021202)41:23<4526::aid-anie4526>3.0.co;2-k.

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50

Zhao, Gui-Ling, Farman Ullah, Luca Deiana, et al. "Dynamic Kinetic Asymmetric Transformation (DYKAT) by Combined Amine- and Transition-Metal-Catalyzed Enantioselective Cycloisomerization." Chemistry - A European Journal 16, no. 5 (2010): 1585–91. http://dx.doi.org/10.1002/chem.200902818.

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