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Journal articles on the topic 'Acylaziridines'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Rubin, Heather, Jennifer Cockrell, and Jeremy B. Morgan. "Scalable Synthesis ofN-Acylaziridines fromN-Tosylaziridines." Journal of Organic Chemistry 78, no. 17 (2013): 8865–71. http://dx.doi.org/10.1021/jo401267j.

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2

Pankova, Alena, and Mikhail Kuznetsov. "Recent Advances in the Chemistry of 2-Acylaziridines." Synthesis 49, no. 23 (2017): 5093–104. http://dx.doi.org/10.1055/s-0036-1590889.

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Abstract:

This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.1 Introduction2 Reactions via C–C Bond Cleavage3 Reactions via C–N Bond Cleavage3.1 Reactions Starting with the Aziridine Ring Opening3.2 Reactions Starting at the Carbonyl Group4 Conclusion

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3

Tangara, Salia, Alice Kanazawa, and Sandrine Py. "The Baldwin Rearrangement: Synthesis of 2-Acylaziridines." European Journal of Organic Chemistry 2017, no. 43 (2017): 6357–64. http://dx.doi.org/10.1002/ejoc.201700920.

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4

Kim, Yongeun, Hyun-Joon Ha, Hoseop Yun, Baeck Kyoung Lee, and Won Koo Lee. "Ring opening of 2-acylaziridines by acid chlorides." Tetrahedron 62, no. 37 (2006): 8844–49. http://dx.doi.org/10.1016/j.tet.2006.06.025.

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5

Gayon, Eric, Olivier Debleds, Marie Nicouleau, et al. "Highly Diastereoselective Baldwin Rearrangement of Isoxazolines intocis-Acylaziridines." Journal of Organic Chemistry 75, no. 17 (2010): 6050–53. http://dx.doi.org/10.1021/jo101273d.

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6

Cockrell, Jennifer, Christopher Wilhelmsen, Heather Rubin, Allen Martin, and Jeremy B. Morgan. "Enantioselective Synthesis and Stereoselective Ring Opening ofN-Acylaziridines." Angewandte Chemie International Edition 51, no. 39 (2012): 9842–45. http://dx.doi.org/10.1002/anie.201204224.

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7

Cockrell, Jennifer, Christopher Wilhelmsen, Heather Rubin, Allen Martin, and Jeremy B. Morgan. "Enantioselective Synthesis and Stereoselective Ring Opening ofN-Acylaziridines." Angewandte Chemie 124, no. 39 (2012): 9980–83. http://dx.doi.org/10.1002/ange.201204224.

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8

Ward, Virginia R., Matthew A. Cooper та A. David Ward. "Synthesis of N-acylaziridines from β-amido selenides". Journal of the Chemical Society, Perkin Transactions 1, № 9 (2001): 944–45. http://dx.doi.org/10.1039/b102468j.

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9

Mita, Tsuyoshi, Ikuo Fujimori, Reiko Wada, Jianfeng Wen, Motomu Kanai, and Masakatsu Shibasaki. "Catalytic Enantioselective Desymmetrization ofmeso-N-Acylaziridines with TMSCN." Journal of the American Chemical Society 127, no. 32 (2005): 11252–53. http://dx.doi.org/10.1021/ja053486y.

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10

Yook, Cheol-Min, Hee-Sung Eum, Hyun-Joon Ha, Kyung-Yeon Kang, and Won-Koo Lee. "Regiochemical Pathway in the Ring Opening of 2-Acylaziridines." Bulletin of the Korean Chemical Society 32, spc8 (2011): 2879–80. http://dx.doi.org/10.5012/bkcs.2011.32.8.2879.

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11

Besbes, Néji. "Regiospecific ring opening of N-acylaziridines by neutral hydrolysis." Tetrahedron Letters 40, no. 36 (1999): 6569–70. http://dx.doi.org/10.1016/s0040-4039(99)00979-x.

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12

Silva, Saúl, and Christopher D. Maycock. "Chemoenzymatic preparation of optically active cyclic 4-hydroxy-acylaziridines." Organic Chemistry Frontiers 4, no. 8 (2017): 1620–23. http://dx.doi.org/10.1039/c7qo00254h.

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13

Eastwood, Frank W., Patrick Perlmutter, and Qi Yang. "Preparation of new 2,4-disubstituted oxazoles from N-acylaziridines." Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1997): 35–42. http://dx.doi.org/10.1039/a604091h.

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14

Ferraris, Dana, William J. Drury, Christopher Cox, and Thomas Lectka. "“Orthogonal” Lewis Acids: Catalyzed Ring Opening and Rearrangement of Acylaziridines." Journal of Organic Chemistry 63, no. 14 (1998): 4568–69. http://dx.doi.org/10.1021/jo980558d.

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15

Kim, Soo Hyun, Sang‐Yun Na, Hyun‐Joon Ha, and Won Koo Lee. "An Efficient Synthesis of 1,3‐Disubstituted Pyrazoles from 2‐Acylaziridines." Asian Journal of Organic Chemistry 8, no. 9 (2019): 1680–86. http://dx.doi.org/10.1002/ajoc.201900233.

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16

Rubin, Heather, Jennifer Cockrell, and Jeremy B. Morgan. "ChemInform Abstract: Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines." ChemInform 45, no. 4 (2014): no. http://dx.doi.org/10.1002/chin.201404099.

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17

Shustov, G. V., F. D. Polyak, G. K. Kadorkina, et al. "Chiroptical properties of the nonplanar amide chromophore in n-acylaziridines." Chemistry of Heterocyclic Compounds 25, no. 1 (1989): 32–39. http://dx.doi.org/10.1007/bf00472614.

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18

Ward, Virginia R., Matthew A. Cooper та A. David Ward. "ChemInform Abstract: Synthesis of N-Acylaziridines from β-Amido Selenides." ChemInform 32, № 34 (2010): no. http://dx.doi.org/10.1002/chin.200134043.

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19

Gayon, Eric, Olivier Debleds, Marie Nicouleau, et al. "ChemInform Abstract: Highly Diastereoselective Baldwin Rearrangement of Isoxazolines into cis-Acylaziridines." ChemInform 41, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.201052101.

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20

Besbes, Neji. "ChemInform Abstract: Regiospecific Ring Opening of N-Acylaziridines by Neutral Hydrolysis." ChemInform 30, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199950046.

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21

EASTWOOD, F. W., P. PERLMUTTER, and Q. YANG. "ChemInform Abstract: Preparation of New 2,4-Disubstituted Oxazoles from N-Acylaziridines." ChemInform 28, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199729116.

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22

Beletskii, E. V., та M. A. Kuznetsov. "Synthesis of oxazoles from α,β-unsaturated carbonyl compounds through 2-acylaziridines". Russian Journal of Organic Chemistry 45, № 8 (2009): 1229–40. http://dx.doi.org/10.1134/s107042800908020x.

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23

Shustov, G. V., G. K. Kadorkina, S. V. Varlamov, A. V. Kachanov, R. G. Kostyanovskii, and A. Rauk. "The nonplanar amide group in N-acylaziridines: conformational behavior and chiroptical properties." Journal of the American Chemical Society 114, no. 5 (1992): 1616–23. http://dx.doi.org/10.1021/ja00031a012.

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24

Ogawa, Yasuyuki, Kiichi Kuroda, and Teruaki Mukaiyama. "Highly Stereoselective Samarium(II) Iodide-Mediated Aldol Reactions of Acylaziridines with Aldehydes." Bulletin of the Chemical Society of Japan 78, no. 7 (2005): 1309–33. http://dx.doi.org/10.1246/bcsj.78.1309.

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25

FERRARIS, D., W. J. III DRURY, C. COX, and T. LECTKA. "ChemInform Abstract: “Orthogonal” Lewis Acids: Catalyzed Ring Opening and Rearrangement of Acylaziridines." ChemInform 29, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199849128.

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26

Beaufour, M., J. C. Cherton, A. Carlin-Sinclair, and S. Hamm. "Delta(2)-oxazolines-1,3 and N-acylaziridines as potential proinsecticides of carboxylic acids." Journal of Chromatography B: Biomedical Sciences and Applications 761, no. 1 (2001): 35–45. http://dx.doi.org/10.1016/s0378-4347(01)00295-x.

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27

Hao, Wei, Xiangyu Wu, James Z. Sun, Juno C. Siu, Samantha N. MacMillan, and Song Lin. "Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes." Journal of the American Chemical Society 139, no. 35 (2017): 12141–44. http://dx.doi.org/10.1021/jacs.7b06723.

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28

Archier-Jay, D., N. Besbes, A. Laurent, E. Laurent, H. Stamm, and R. Tardivel. "Reductive ring opening of N-acylaziridines : Different outcomes of chemical and electrochemical reactions." Tetrahedron Letters 30, no. 17 (1989): 2271–72. http://dx.doi.org/10.1016/s0040-4039(00)99669-2.

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29

Miyamoto, Yoshiaki, Norihiro Wada, Takahiro Soeta, Shuhei Fujinami, Katsuhiko Inomata, and Yutaka Ukaji. "One-Pot Stereoselective Synthesis of 2-Acylaziridines and 2-Acylpyrrolidines fromN-(Propargylic)hydroxylamines." Chemistry - An Asian Journal 8, no. 4 (2013): 824–31. http://dx.doi.org/10.1002/asia.201201180.

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30

Lattanzi, Alessandra, та Giorgio Della Sala. "Desymmetrization of meso-N-Acylaziridines with Benzenethiols Promoted by α,α-Diaryl-L-prolinols". European Journal of Organic Chemistry 2009, № 12 (2009): 1845–48. http://dx.doi.org/10.1002/ejoc.200900095.

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31

SHUSTOV, G. V., G. K. KADORKINA, S. V. VARLAMOV, A. V. KACHANOV, R. G. KOSTYANOVSKY, and A. RAUK. "ChemInform Abstract: The Nonplanar Amide Group in N-Acylaziridines: Conformational Behavior and Chiroptical Properties." ChemInform 23, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199226042.

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32

Wada, Norihiro, Kentaro Kaneko, Yutaka Ukaji, and Katsuhiko Inomata. "Selective Transformation ofN-(Propargylic)hydroxylamines into 4-Isoxazolines and Acylaziridines Promoted by Metal Salts." Chemistry Letters 40, no. 5 (2011): 440–42. http://dx.doi.org/10.1246/cl.2011.440.

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33

Buijnsters, Peter J. J. A., Martinus C. Feiters, Roeland J. M. Nolte, Nico A. J. M. Sommerdijk, and Binne Zwanenburg. "Autocatalytic ring opening of N-acylaziridines. Complete control over regioselectivity by orientation at interfaces." Chemical Communications, no. 3 (2001): 269–70. http://dx.doi.org/10.1039/b009294k.

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34

MALL, T., B. BUCHHOLZ, and H. STAMM. "ChemInform Abstract: Aziridines. Part 63. Friedel-Crafts Reactions of Some N-Acylaziridines: Oxazolins as Intermediates." ChemInform 25, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199443149.

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35

Lin, Pen-Yuan, Konstantinos Bellos, J�rgen Werry, et al. "Aziridines. 69. Reactions of N-Acylaziridines with Sodium Metal and Sodium Naphthalenide. Elimination of olefines." Journal f�r Praktische Chemie/Chemiker-Zeitung 338, no. 1 (1996): 270–78. http://dx.doi.org/10.1002/prac.19963380153.

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36

Tangara, Salia, Alice Kanazawa, and Sandrine Py. "Cover Feature: The Baldwin Rearrangement: Synthesis of 2-Acylaziridines (Eur. J. Org. Chem. 43/2017)." European Journal of Organic Chemistry 2017, no. 43 (2017): 6355. http://dx.doi.org/10.1002/ejoc.201701548.

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37

Silva, Saúl, Paula Rodrigues, Isabel Bento, and Christopher D. Maycock. "The Aza-Wharton Reaction: Syntheses of Cyclic Allylic Amines and Vicinal Hydroxyamines from the Respective Acylaziridines." Journal of Organic Chemistry 80, no. 6 (2015): 3067–74. http://dx.doi.org/10.1021/jo5029387.

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38

Buijnsters, Peter J. J. A., Martinus C. Feiters, Roeland J. M. Nolte, Nico A. J. M. Sommerdijk, and Binne Zwanenburg. "ChemInform Abstract: Autocatalytic Ring Opening of N-Acylaziridines. Complete Control over Regioselectivity by Orientation at Interfaces." ChemInform 32, no. 19 (2001): no. http://dx.doi.org/10.1002/chin.200119149.

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39

Miyamoto, Yoshiaki, Norihiro Wada, Takahiro Soeta, Shuhei Fujinami, Katsuhiko Inomata, and Yutaka Ukaji. "ChemInform Abstract: One-Pot Stereoselective Synthesis of 2-Acylaziridines and 2-Acylpyrrrolidines from N-(Propargylic)hydroxylamines." ChemInform 44, no. 34 (2013): no. http://dx.doi.org/10.1002/chin.201334111.

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40

Wada, Norihiro, Kentaro Kaneko, Yutaka Ukaji, and Katsuhiko Inomata. "ChemInform Abstract: Selective Transformation of N-(Propargylic)hydroxylamines into 4-Isoxazolines and Acylaziridines Promoted by Metal Salts." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142126.

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41

Ishikawa, Teruhiko, Takayuki Kudoh, Juri Yoshida, Ayako Yasuhara, Shinobu Manabe, and Seiki Saito. "Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines: Dramatic Rate Acceleration with Very High Substrate Tolerance." Organic Letters 4, no. 11 (2002): 1907–10. http://dx.doi.org/10.1021/ol025906j.

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42

Hayashi, Masahiko, Kazuyuki Ono, Haruhisa Hoshimi, and Nobuki Oguni. "Asymmetric ring opening reactions of symmetrical N-acylaziridines with thiols catalyzed by chiral dialkyl tartrate-diethylzinc complexes." Tetrahedron 52, no. 23 (1996): 7817–32. http://dx.doi.org/10.1016/0040-4020(96)00370-5.

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43

Besbes, Néji, Houyem Jellali, Patrick Pale, Ezzeddine Srasra, and Mohamed Lotfi Efrit. "Transformations de N-acylaziridines catalysées par des supports à base de silice et d’alumine : une élucidation mécanistique." Comptes Rendus Chimie 13, no. 3 (2010): 358–64. http://dx.doi.org/10.1016/j.crci.2009.09.014.

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44

Molander, G. "Reduction of 2-Acylaziridines by Samarium(II) Iodide. An Efficient and Regioselective Route to β-Amino Carbonyl Compounds." Tetrahedron 53, № 26 (1997): 8887–912. http://dx.doi.org/10.1016/s0040-4020(97)00576-0.

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45

Molander, Gary A., та Peter J. Stengel. "Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds". Tetrahedron 53, № 26 (1997): 8887–912. http://dx.doi.org/10.1016/s0040-4020(97)90399-9.

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46

LIN, P. Y., K. BELLOS, J. WERRY, et al. "ChemInform Abstract: Aziridines. Part 69. Reactions of N-Acylaziridines with Sodium Metal and Sodium Naphthalenide. Elimination of Olefins." ChemInform 27, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199634096.

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47

Hayashi, Masahiko, Kazuyuki Ono, Haruhisa Hoshimi, and Nobuki Oguni. "Novel asymmetric ring-opening reactions of symmetrical N-acylaziridines with arenethiols catalysed by chiral dialkyl tartrate–diethylzinc complexes." J. Chem. Soc., Chem. Commun., no. 23 (1994): 2699–700. http://dx.doi.org/10.1039/c39940002699.

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48

Silva, Saul, Paula Rodrigues, Isabel Bento, and Christopher D. Maycock. "ChemInform Abstract: The Aza-Wharton Reaction: Syntheses of Cyclic Allylic Amines and Vicinal Hydroxyamines from the Respective Acylaziridines." ChemInform 46, no. 31 (2015): no. http://dx.doi.org/10.1002/chin.201531040.

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49

Molander, Gary A., and Peter J. Stengel. "Reduction of 2-Acylaziridines by Samarium(II) Iodide. An Efficient and Regioselective Route to .beta.-Amino Ketones and Esters." Journal of Organic Chemistry 60, no. 21 (1995): 6660–61. http://dx.doi.org/10.1021/jo00126a005.

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50

HAYASHI, M., K. ONO, H. HOSHIMI, and N. OGUNI. "ChemInform Abstract: Asymmetric Ring Opening Reactions of Symmetrical N-Acylaziridines with Thiols Catalyzed by Chiral Dialkyl Tartrate-Diethylzinc Complexes." ChemInform 27, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199639068.

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