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Journal articles on the topic 'Asymmetric aziridination'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Pellissier, Hélène. "Recent developments in asymmetric aziridination." Tetrahedron 66, no. 8 (2010): 1509–55. http://dx.doi.org/10.1016/j.tet.2009.11.089.

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2

Pellissier, Hélène. "Recent Developments in Asymmetric Aziridination." Advanced Synthesis & Catalysis 356, no. 9 (2014): 1899–935. http://dx.doi.org/10.1002/adsc.201400312.

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3

Roma, Elia, Eleonora Tosi, Martina Miceli, and Tecla Gasperi. "Asymmetric Organocatalytic Aziridination: Recent Advances." Asian Journal of Organic Chemistry 7, no. 12 (2018): 2357–67. http://dx.doi.org/10.1002/ajoc.201800431.

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4

Pesciaioli, Fabio, Francesco De Vincentiis, Patrizia Galzerano, et al. "Organocatalytic Asymmetric Aziridination of Enones." Angewandte Chemie 120, no. 45 (2008): 8831–34. http://dx.doi.org/10.1002/ange.200803647.

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5

Pesciaioli, Fabio, Francesco De Vincentiis, Patrizia Galzerano, et al. "Organocatalytic Asymmetric Aziridination of Enones." Angewandte Chemie International Edition 47, no. 45 (2008): 8703–6. http://dx.doi.org/10.1002/anie.200803647.

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6

Wipf, Peter, and Michael A. Lyon. "Catalytic asymmetric aziridination of aryl imines." Arkivoc 2007, no. 12 (2007): 91–98. http://dx.doi.org/10.3998/ark.5550190.0008.c07.

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7

Kawabata, H., K. Omura, and T. Katsuki. "Ru(II)-Salen-Catalyzed Asymmetric Aziridination." Synfacts 2006, no. 5 (2006): 0457. http://dx.doi.org/10.1055/s-2006-934349.

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8

De Vincentiis, Francesco, Giorgio Bencivenni, Fabio Pesciaioli, et al. "Asymmetric Catalytic Aziridination of Cyclic Enones." Chemistry - An Asian Journal 5, no. 7 (2010): 1652–56. http://dx.doi.org/10.1002/asia.201000040.

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9

Gupta, Anil K., Munmun Mukherjee, and William D. Wulff. "Multicomponent Catalytic Asymmetric Aziridination of Aldehydes." Organic Letters 13, no. 21 (2011): 5866–69. http://dx.doi.org/10.1021/ol202472z.

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10

Wulff, William D., Yong Guan, Zhenjie Lu, Xiaopeng Yin, Aliakbar Mohammadlou, and Richard J. Staples. "Catalytic Asymmetric Aziridination of Benzhydryl Imines and Diazoacetate Esters with BOROX Catalysts from 3,3′-Disubstituted VANOL Ligands." Synthesis 52, no. 14 (2020): 2073–91. http://dx.doi.org/10.1055/s-0039-1690860.

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This work details the synthesis of 22 new chiral VANOL ligands that differ by the nature of the substituent in the 3- and 3′-positions of the ligand. These ligands were incorporated into boroxinate catalysts that were used to screen the catalytic asymmetric aziridination of benzhydryl imines with ethyl diazoacetate. Each catalyst was screened in the reaction of imines generated from benzaldehyde and cyclohexanecarboxaldehyde and some with 4-nitro- and 4-methoxybenzaldehyde. In addition, the first report of the effect of the ester substituent of the diazoacetate ester on the asymmetric inductio

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11

Pellissier, Helene. "ChemInform Abstract: Recent Developments in Asymmetric Aziridination." ChemInform 41, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.201021241.

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12

Pellissier, Helene. "ChemInform Abstract: Recent Developments in Asymmetric Aziridination." ChemInform 45, no. 35 (2014): no. http://dx.doi.org/10.1002/chin.201435251.

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13

Aggarwal, Varinder, Alison Thompson, Ray Jones, and Mike Standen. "Catalytic and Asymmetric Aziridination using Sulfur Ylides." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (1997): 361–62. http://dx.doi.org/10.1080/10426509708043981.

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14

Aggarwal, Varinder K., Alison Thompson, Ray V. H. Jones, and Mike C. H. Standen. "Catalytic and Asymmetric Aziridination using Sulfur Ylides." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (1997): 361–62. http://dx.doi.org/10.1080/10426509708545549.

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15

Wulff, W., Y. Deng, Y. Lee, and C. Newman. "Asymmetric Aziridination to Provide Aziridinyl Vinyl Ketones." Synfacts 2007, no. 7 (2007): 0737. http://dx.doi.org/10.1055/s-2007-968671.

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16

Halskov, Kim Søholm, Tricia Naicker, Magnus E. Jensen, and Karl Anker Jørgensen. "Organocatalytic asymmetric remote aziridination of 2,4-dienals." Chemical Communications 49, no. 57 (2013): 6382. http://dx.doi.org/10.1039/c3cc43506g.

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17

McGarrigle, Eoghan, Varinder Aggarwal, Martin Fearraigh, Johnathan Matlock, and Ona Illa. "Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination." Synthesis 50, no. 17 (2018): 3337–43. http://dx.doi.org/10.1055/s-0037-1609580.

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The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.

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18

Tao, Jingran, Li-Mei Jin, and X. Peter Zhang. "Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis." Beilstein Journal of Organic Chemistry 10 (June 4, 2014): 1282–89. http://dx.doi.org/10.3762/bjoc.10.129.

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The Co(II) complex of a new D 2-symmetric chiral porphyrin 3,5-DiMes-QingPhyrin, [Co(P6)], can catalyze asymmetric aziridination of alkenes with bis(2,2,2-trichloroethyl)phosphoryl azide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromatic olefins, producing the corresponding N-phosphorylaziridines in good to excellent yields (up to 99%) with moderate to high enantioselectivities (up to 85% ee). In addition to mild reaction conditions and generation of N2 as the only byproduct, this new metalloradical catalytic system is highlighte

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19

Deiana, Luca, Pawel Dziedzic, Gui‐Ling Zhao та ін. "Catalytic Asymmetric Aziridination of α,β‐Unsaturated Aldehydes". Chemistry – A European Journal 17, № 28 (2011): 7904–17. http://dx.doi.org/10.1002/chem.201100042.

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20

Gupta, Anil K., Munmun Mukherjee, and William D. Wulff. "ChemInform Abstract: Multicomponent Catalytic Asymmetric Aziridination of Aldehydes." ChemInform 43, no. 12 (2012): no. http://dx.doi.org/10.1002/chin.201212086.

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21

De Vincentiis, Francesco, Giorgio Bencivenni, Fabio Pesciaioli, et al. "ChemInform Abstract: Asymmetric Catalytic Aziridination of Cyclic Enones." ChemInform 41, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.201043096.

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22

Jones, Jess E., Joshua V. Ruppel, Guang-Yao Gao, Thomas M. Moore, and X. Peter Zhang. "Cobalt-Catalyzed Asymmetric Olefin Aziridination with Diphenylphosphoryl Azide." Journal of Organic Chemistry 73, no. 18 (2008): 7260–65. http://dx.doi.org/10.1021/jo801151x.

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23

Wang, Zhonghua, Feng Li, Lei Zhao, Qiuqin He, Fener Chen, and Chen Zheng. "An efficient enantioselective synthesis of florfenicol via asymmetric aziridination." Tetrahedron 67, no. 47 (2011): 9199–203. http://dx.doi.org/10.1016/j.tet.2011.09.052.

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24

Khantikaew, Itsara, Masato Takahashi, Takuya Kumamoto, Noriyuki Suzuki, and Tsutomu Ishikawa. "Synthesis of (−)-benzolactam-V8 by application of asymmetric aziridination." Tetrahedron 68, no. 3 (2012): 878–82. http://dx.doi.org/10.1016/j.tet.2011.11.033.

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25

Desai, Aman A., and William D. Wulff. "Controlled Diastereo- and Enantioselection in a Catalytic Asymmetric Aziridination." Journal of the American Chemical Society 132, no. 38 (2010): 13100–13103. http://dx.doi.org/10.1021/ja1038648.

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26

Li, An-Hu, Li-Xin Dai, and Varinder K. Aggarwal. "Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and Rearrangement†." Chemical Reviews 97, no. 6 (1997): 2341–72. http://dx.doi.org/10.1021/cr960411r.

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27

Deng, Yonghong, Young Rok Lee, Cory A. Newman, and William D. Wulff. "Aziridinyl Vinyl Ketones from the Asymmetric Catalytic Aziridination Reaction." European Journal of Organic Chemistry 2007, no. 13 (2007): 2068–71. http://dx.doi.org/10.1002/ejoc.200601126.

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28

Halskov, Kim Soeholm, Tricia Naicker, Magnus E. Jensen, and Karl Anker Joergensen. "ChemInform Abstract: Organocatalytic Asymmetric Remote Aziridination of 2,4-Dienals." ChemInform 44, no. 43 (2013): no. http://dx.doi.org/10.1002/chin.201343085.

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29

Hajra, Saumen, Sk Md Samim Akhtar, and Sk Mohammad Aziz. "Catalytic asymmetric aminolactonization of 1,2-disubstituted alkenoic acid esters: Efficient construction of aminolactones with an all-carbon quaternary stereo-centre." Chem. Commun. 50, no. 52 (2014): 6913–16. http://dx.doi.org/10.1039/c4cc01944j.

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30

Li, Zhen, Kathryn R. Conser, and Eric N. Jacobsen. "Asymmetric alkene aziridination with readily available chiral diimine-based catalysts." Journal of the American Chemical Society 115, no. 12 (1993): 5326–27. http://dx.doi.org/10.1021/ja00065a067.

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31

Noda, Kenji, Naoki Hosoya, Ryo Irie, Yoshio Ito, and Tsutomu Katsuki. "Asymmetric Aziridination by Using Optically Active (Salen)manganese(III) Complexes." Synlett 1993, no. 07 (1993): 469–71. http://dx.doi.org/10.1055/s-1993-22494.

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32

Deiana, Luca, Pawel Dziedzic, Gui-Ling Zhao та ін. "ChemInform Abstract: Catalytic Asymmetric Aziridination of α,β-Unsaturated Aldehydes." ChemInform 42, № 44 (2011): no. http://dx.doi.org/10.1002/chin.201144088.

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33

Mukherjee, Munmun, Yubai Zhou, Anil K. Gupta, Yong Guan, and William D. Wulff. "A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination." European Journal of Organic Chemistry 2014, no. 7 (2014): 1386–90. http://dx.doi.org/10.1002/ejoc.201301766.

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34

Aggarwal, Varinder K., J. Gair Ford, Alison Thompson, John Studley, Ray V. H. Jones, and Robin Fieldhouse. "ChemInform Abstract: Sulfur Ylide Mediated Catalytic Asymmetric Epoxidation and Aziridination." ChemInform 31, no. 41 (2000): no. http://dx.doi.org/10.1002/chin.200041236.

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35

Ma, Linge, Da-Ming Du, and Jiaxi Xu. "Asymmetric aziridination of 1,3-dienes catalyzed by bisoxazoline-copper complexes." Chirality 18, no. 8 (2006): 575–80. http://dx.doi.org/10.1002/chir.20282.

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36

Ranocchiari, Marco, and Antonio Mezzetti. "Ru/PNNP-Catalyzed Asymmetric Imine Aziridination by Diazo Ester Activation." Organometallics 28, no. 13 (2009): 3611–13. http://dx.doi.org/10.1021/om900415g.

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37

Antilla, Jon C., and William D. Wulff. "Catalytic Asymmetric Aziridination with a Chiral VAPOL−Boron Lewis Acid." Journal of the American Chemical Society 121, no. 21 (1999): 5099–100. http://dx.doi.org/10.1021/ja9905187.

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38

Wulff, William, Yu Zhang, and Zhenjie Lu. "Catalytic Asymmetric Aziridination with Catalysts Derived from VAPOL and VANOL." Synlett 2009, no. 17 (2009): 2715–39. http://dx.doi.org/10.1055/s-0029-1217979.

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39

Page, Philip, Céline Bordogna, Ian Strutt, Yohan Chan, and Benjamin Buckley. "Asymmetric Aziridination of Chalcone Promoted by Binaphthalene-Based Chiral Amines." Synlett 24, no. 16 (2013): 2067–72. http://dx.doi.org/10.1055/s-0033-1339643.

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40

Flock, Susanne, and Herbert Frauenrath. "Asymmetric synthesis of 4H-1,3-dioxins and investigations in the metal catalyzed aziridination: aziridination versus insertion and stereoselective course." Arkivoc 2007, no. 10 (2007): 245–59. http://dx.doi.org/10.3998/ark.5550190.0008.a15.

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41

Rajeev, Ramanan, and Raghavan B. Sunoj. "Mechanism and electronic effects in nitrogen ylide-promoted asymmetric aziridination reaction." Organic & Biomolecular Chemistry 9, no. 7 (2011): 2123. http://dx.doi.org/10.1039/c0ob00955e.

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42

Subbarayan, Velusamy, Joshua V. Ruppel, Shifa Zhu, Jason A. Perman, and X. Peter Zhang. "Highly asymmetric cobalt-catalyzed aziridination of alkenes with trichloroethoxysulfonyl azide (TcesN3)." Chemical Communications, no. 28 (2009): 4266. http://dx.doi.org/10.1039/b905727g.

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43

Zhu, Yingguang, Qian Wang, Richard G. Cornwall, and Yian Shi. "Organocatalytic Asymmetric Epoxidation and Aziridination of Olefins and Their Synthetic Applications." Chemical Reviews 114, no. 16 (2014): 8199–256. http://dx.doi.org/10.1021/cr500064w.

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44

LI, A. H., L. X. DAI, and V. K. AGGARWAL. "ChemInform Abstract: Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and Rearrangement." ChemInform 28, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199752316.

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45

Desai, Aman A., and William D. Wulff. "ChemInform Abstract: Controlled Diastereo- and Enantioselection in a Catalytic Asymmetric Aziridination." ChemInform 42, no. 11 (2011): no. http://dx.doi.org/10.1002/chin.201111112.

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46

Li, An-Hu, Yong-Gui Zhou, Li-Xin Dai, Xue-Long Hou, Li-Jun Xia, and Lin Lin. "Asymmetric Aziridination over Ylides: Highly Stereoselective Synthesis of Acetylenyl-N-sulfonylaziridines." Angewandte Chemie International Edition in English 36, no. 12 (1997): 1317–19. http://dx.doi.org/10.1002/anie.199713171.

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47

Aggarwal, Varinder K., Alison Thompson, Ray V. H. Jones, and Mike C. H. Standen. "Novel Catalytic and Asymmetric Process for Aziridination Mediated by Sulfur Ylides." Journal of Organic Chemistry 61, no. 24 (1996): 8368–69. http://dx.doi.org/10.1021/jo961754s.

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48

Janardanan, Deepa, and Raghavan B. Sunoj. "Enantio- and Diastereoselectivities in Chiral Sulfur Ylide Promoted Asymmetric Aziridination Reactions." Journal of Organic Chemistry 73, no. 21 (2008): 8163–74. http://dx.doi.org/10.1021/jo800652c.

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49

dos Santos, Deborah A., Allan R. da Silva, Javier Ellena, Cecilia C. P. da Silva, Marcio W. Paixão, and Arlene G. Corrêa. "Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction." Synthesis 52, no. 07 (2019): 1076–86. http://dx.doi.org/10.1055/s-0039-1690774.

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Peptidomimetics containing an aziridine moiety have been reported as potent cysteine protease inhibitors. In this sense, the development of stereoselective and sustainable synthetic strategies to obtain three-membered N-heterocyclic compounds has gained importance in the last decades. In this work, an efficient method was designed to achieve highly functionalized aziridine peptidomimetics via a sequential reaction, which involves the organocatalytic aziridination of α,β-unsaturated aldehydes followed by the Passerini multicomponent reaction in an environmentally friendly solvent mixture (ethan

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50

Xue, Zheng, Veronica M. Dee, Louisa J. Hope-Weeks, Bruce R. Whittlesey, and Michael F. Mayer. "Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides." Arkivoc 2010, no. 7 (2010): 65–80. http://dx.doi.org/10.3998/ark.5550190.0011.706.

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