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Journal articles on the topic 'Chiral nitronic acid'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Fu-An Kang and Cheng-Lie Yin. "Studies on the chemistry of the chiral nitronic acid and nitronic esters." Tetrahedron: Asymmetry 8, no. 21 (1997): 3585–89. http://dx.doi.org/10.1016/s0957-4166(97)00478-3.

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2

Lei, Lei Zhang, and Qiang Feng Zhi. "The stereoselective C-alkylation of chiral nitronic acid (4S*,5R)-(+)-4-(6-nitro6-carbethoxymethyl)-5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furano." Journal of Indian Chemical Society Vol. 91, Jul 2014 (2014): 1335–39. https://doi.org/10.5281/zenodo.5726355.

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State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2 Nanwei Rd., Xicheng Dist., Beijing 100050, P. R. China <em>E-mail</em> : fengzhq@imm.ac.cn <em>Manuscript received online 29 October 2013, accepted 17 February 2014</em> The stereoselective C-alkylation of a chiral nitronic acid (4<em>S</em><sup>*</sup>,5R)-(+)-4-(6-nitro-6-carbethoxymethyl)-5-[(1<em>R</em>)- menthyloxy]-3,4-dihydro-2(<em>5H</em>)-furanone which was generally alkylated by alkyl halide giving single <

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3

Aurich, Hans Günter, Christian Gentes та Ulrich Sievers. "Darstellung chiraler heterocyclischer β-Aminosäureester / Preparation of Chiral Heterocyclic Esters of β-Amino Acids". Zeitschrift für Naturforschung B 54, № 4 (1999): 519–31. http://dx.doi.org/10.1515/znb-1999-0416.

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Chiral β-amino alcohols were successively prone to N-benzylation, O-allylation and oxidation of the resulting benzylamino group to give nitrones 3 which on hydrolysis afforded chiral hydroxylamines HO-NH-CH(R)-CH2-O-CH2-CH=CH2 ((S)-4: R = Me, Bn, iPr. (R)-4: R = Et). Swern oxidation of methyl 2,2-dimethyl-3-hydroxypropionate (16) and treatment of the resulting aldehyde 17 with hydroxylamines (S)-4b (R = Bn) or (R)-4d (R = Et) provided nitrones 18 that underwent an intramolecular 1,3-dipolar cycloaddition on heating yielding the bicyclic β-amino-acid esters 19b and ent-19d, respectively.Reducti

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4

Jin, Yuan, Yasuhiro Honma, Hisashi Morita, Masamichi Miyagawa, and Takahiko Akiyama. "Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid." Synlett 30, no. 13 (2019): 1541–45. http://dx.doi.org/10.1055/s-0039-1690108.

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A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

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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

Xu, Xichen, Yingjun Zhao, and Di Wu. "Sc(OTf)3-Catalyzed [3+2]-Cycloaddition of Diazoacetoacetate Enones and N-Aryl Nitrones: Diastereoselective Synthesis of Functionalized Isoxazolidines with Three Contiguous Stereogenic Centers." Synthesis 54, no. 09 (2022): 2213–24. http://dx.doi.org/10.1055/s-0041-1737804.

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AbstractA catalytic [3+2]-cycloaddition using Sc(OTf)3 as a Lewis acid catalyst is developed. This catalytic 1,3-dipolar cycloaddition diastereoselectively transforms diazoacetoacetate enones and N-aryl nitrones into highly functionalized isoxazolidines bearing three contiguous chiral centers. The feasibility of the uncatalyzed 1,3-dipolar cycloaddition is postulated by DFT calculations and substantiated experimentally.

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7

Li, Feng, Zhao-Ming Li, Hua Yang та Volker Jäger. "New Approaches to Branched β-Amino α-Hydroxy Acids, Taxol Side-chain Analogs". Zeitschrift für Naturforschung B 63, № 4 (2008): 431–46. http://dx.doi.org/10.1515/znb-2008-0410.

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AbstractThe phenylisothreonine derivatives, taxol side-chain analogs, were synthesized by two routes, one based on the highly stereoselective addition of a phenyl Grignard reagent to the L-threose-derived nitrone 7, and the other using asymmetric α-alkoxyallylation of the ketimine 20 with chiral allyl boron reagents.

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8

Kitanosono, Taku, Pengyu Xu, and Shū Kobayashi. "Chiral Lewis acids integrated with single-walled carbon nanotubes for asymmetric catalysis in water." Science 362, no. 6412 (2018): 311–15. http://dx.doi.org/10.1126/science.aap7883.

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The development of highly reactive and stereoselective catalytic systems is required not only to improve existing synthetic methods but also to invent distinct chemical reactions. Herein, a homogenized combination of nickel-based Lewis acid–surfactant-combined catalysts and single-walled carbon nanotubes is shown to exhibit substantial activity in water. In addition to the enhanced reactivity, stereoselective performance and long-term stability were demonstrated in asymmetric conjugate addition reactions of aldoximes to furnish chiral nitrones in high yields with excellent selectivities. The p

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9

Hashimoto, Takuya, Masato Omote, Taichi Kano, and Keiji Maruoka. "Asymmetric 1,3-Dipolar Cycloadditions of Nitrones and Methacrolein Catalyzed by Chiral Bis-Titanium Lewis Acid: A Dramatic Effect ofN-Substituent on Nitrone." Organic Letters 9, no. 23 (2007): 4805–8. http://dx.doi.org/10.1021/ol702123n.

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10

Blanáriková, Iva, Lubor Fišera, Zuzana Kopanicková, Piotr Salanski, Janusz Jurczak, and Christian Hametner. "Synthesis of chiral amino acid - derived nitrones and 1,3-dipolar cycloadditions with acrylic acid methyl ester." Arkivoc 2001, no. 5 (2005): 51–59. http://dx.doi.org/10.3998/ark.5550190.0002.507.

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11

Honda, Kazuya, and Koichi Mikami. "Asymmetric “Acetylenic” [3+2] Cycloaddition of Nitrones Catalyzed by Cationic Chiral PdII Lewis Acid." Chemistry - An Asian Journal 13, no. 19 (2018): 2838–41. http://dx.doi.org/10.1002/asia.201801016.

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12

Kawate, Tomohiko, Hideki Yamada, Miyako Matsumizu, Atsushi Nishida, and Masako Nakagawa. "Enantioselective Pictet-Spengler Reaction of Nitrones Derived from Nb-Hydroxytryptamine with Aldehydes Catalyzed by Chiral Brønsted Acid-Assisted Lewis Acids." Synlett 1997, no. 7 (1997): 761–62. http://dx.doi.org/10.1055/s-1997-5784.

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13

Thiverny, Maryse, Christian Philouze, Pierre Yves Chavant, and Véronique Blandin. "MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis: the cycloaddition approach." Org. Biomol. Chem. 8, no. 4 (2010): 864–72. http://dx.doi.org/10.1039/b918612c.

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14

Di Gioia, Maria Luisa, Antonella Leggio, Adolfo Le Pera, et al. "Synthesis of Chiral Nitrones from N‐Fmoc Amino Acids and N‐Fmoc Dipeptides." Synthetic Communications 34, no. 18 (2004): 3325–34. http://dx.doi.org/10.1081/scc-200030575.

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15

Wei, Weilin, Masato Kobayashi, Yutaka Ukaji, and Katsuhiko Inomata. "Asymmetric Addition of Alkynylzinc Reagents to Nitrones Utilizing Tartaric Acid Ester as a Chiral Auxiliary." Chemistry Letters 35, no. 2 (2006): 176–77. http://dx.doi.org/10.1246/cl.2006.176.

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16

KAWATE, T., H. YAMADA, M. MATSUMIZU, A. NISHIDA, and M. NAKAGAWA. "ChemInform Abstract: Enantioselective Pictet-Spengler Reaction of Nitrones Derived from Nb- Hydroxytryptamine with Aldehydes Catalyzed by Chiral Broensted Acid- Assisted Lewis Acids." ChemInform 28, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199746051.

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17

Rehák, Juraj, Lubor Fišera, and Nada Prónayová. "Samarium diiodide-induced reductive coupling of chiral nitrones prepared from D-isoascorbic acid with methyl acrylate." Arkivoc 2009, no. 6 (2009): 146–57. http://dx.doi.org/10.3998/ark.5550190.0010.615.

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18

Ukaji, Yutaka, Yuuko Shimizu, Yuuichi Kenmoku, Alauddin Ahmed, and Katsuhiko Inomata. "Catalytic Asymmetric Addition Reaction of Dialkylzinc to Nitrone Utilizing Tartaric Acid Ester as a Chiral Auxiliary." Chemistry Letters 26, no. 1 (1997): 59–60. http://dx.doi.org/10.1246/cl.1997.59.

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19

Thiverny, Maryse, Christian Philouze, Pierre Yves Chavant, and Veronique Blandin. "ChemInform Abstract: MiPNO, a New Chiral Cyclic Nitrone for Enantioselective Amino Acid Synthesis: The Cycloaddition Approach." ChemInform 41, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.201025020.

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20

Hashimoto, Takuya, Masato Omote, and Keiji Maruoka. "6,6′-Substituent effect of BINOL in bis-titanium chiral Lewis acid catalyzed 1,3-dipolar cycloaddition of nitrones." Organic & Biomolecular Chemistry 6, no. 13 (2008): 2263. http://dx.doi.org/10.1039/b804987d.

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21

Kawakami, Toru, Hiroaki Ohtake, Hiroaki Arakawa, Takahiro Okachi, Yasushi Imada та Shun-Ichi Murahashi. "Asymmetric Synthesis ofβ-Amino Acids by Addition of Chiral Enolates to Nitrones viaN-Acyloxyiminium Ions". Bulletin of the Chemical Society of Japan 73, № 11 (2000): 2423–44. http://dx.doi.org/10.1246/bcsj.73.2423.

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22

Murahashi, Shun-Ichi, Yasushi Imada, Masahiko Kohno та Toru Kawakami. "Asymmetric 1,3-Dipolar Cycloaddition of Cyclic Nitrones to Crotonic Acid Derivatives Bearing Chiral Auxiliaries. Synthesis of Optically Active β-Amino Acids, (+)-Sedridine, and (+)-Hygroline". Synlett 1993, № 06 (1993): 395–96. http://dx.doi.org/10.1055/s-1993-22467.

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23

Kano, Taichi, Takuya Hashimoto, and Keiji Maruoka. "Asymmetric 1,3-Dipolar Cycloaddition Reaction of Nitrones and Acrolein with a Bis-Titanium Catalyst as Chiral Lewis Acid." Journal of the American Chemical Society 127, no. 34 (2005): 11926–27. http://dx.doi.org/10.1021/ja0523284.

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24

Pernet-Poil-Chevrier, Astrid, Frédéric Cantagrel, Karel Le Jeune, Christian Philouze та Pierre Yves Chavant. "New chiral nitrones as precursors of α,α-disubstituted amino-acids, according to the SRS principle". Tetrahedron: Asymmetry 17, № 13 (2006): 1969–74. http://dx.doi.org/10.1016/j.tetasy.2006.06.046.

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25

UKAJI, Y., Y. SHIMIZU, Y. KENMOKU, A. AHMED, and K. INOMATA. "ChemInform Abstract: Catalytic Asymmetric Addition Reaction of Dialkylzinc to Nitrone Utilizing Tartaric Acid Ester as a Chiral Auxiliary." ChemInform 28, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199726033.

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26

Kiguchi, Toshiko, Mitsuko Shirakawa, Rina Honda, Ichiya Ninomiya, and Takeaki Naito. "Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile." Tetrahedron 54, no. 51 (1998): 15589–606. http://dx.doi.org/10.1016/s0040-4020(98)01012-6.

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27

MURAHASHI, S., Y. IMADA, M. KOHNO та T. KAWAKAMI. "ChemInform Abstract: Asymmetric 1,3-Dipolar Cycloaddition of Cyclic Nitrones to Crotonic Acid Derivatives Bearing Chiral Auxiliaries. Synthesis of Optically Active β-Amino Acids, (+)-Sedridine (I), and (+)-Hygroline (II)." ChemInform 25, № 5 (2010): no. http://dx.doi.org/10.1002/chin.199405174.

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28

Murahashi, Shun-Ichi, Yasushi Imada, Toru Kawakami, Kazuhito Harada, Yoshiharu Yonemushi та Naomi Tomita. "Enantioselective Addition of Ketene Silyl Acetals to Nitrones Catalyzed by Chiral Titanium Complexes. Synthesis of Optically Activeβ-Amino Acids". Journal of the American Chemical Society 124, № 12 (2002): 2888–89. http://dx.doi.org/10.1021/ja0176649.

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29

Kawakami, Toru, Hiroaki Ohtake, Hiroaki Arakawa, Takahiro Okachi, Yasushi Imada та Shun-Ichi Murahashi. "ChemInform Abstract: Asymmetric Synthesis of β-Amino Acids by Addition of Chiral Enolates to Nitrones via N-Acyloxyiminium Ions." ChemInform 32, № 9 (2001): no. http://dx.doi.org/10.1002/chin.200109083.

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30

Praly, Jean-Pierre, Kaiss Aouadi, Sébastien Vidal, and Moncef Msaddek. "Cycloadditions of Chiral Nitrones to Racemic 3-Substituted Butenes: A Direct Access with Kinetic Resolution to Enantiopure Dihydroxylated Amino Acids." Synlett 2006, no. 19 (2006): 3299–303. http://dx.doi.org/10.1055/s-2006-951534.

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31

Merino, Pedro, Santiago Franco, Francisco L. Merchan та Tomas Tejero. "Asymmetric Addition Reactions of Lithium (Trimethylsilyl)acetylide with Chiral α-Amino Nitrones. Synthesis of Diastereomerically PureN-Hydroxy-α-amino Acids†". Journal of Organic Chemistry 63, № 16 (1998): 5627–30. http://dx.doi.org/10.1021/jo9714775.

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32

Dondoni, A., F. Junquera, F. L. Merchan, P. Merino та T. Tejero. "Addition of 2-Lithiofuran to Chiral α-Alkoxy Nitrones; a Stereoselective Approach to α-Epimeric β-Alkoxy-α-amino Acids". Synthesis 1994, № 12 (1994): 1450–56. http://dx.doi.org/10.1055/s-1994-25712.

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33

Johannesen, Sine A., Silvia Albu, Rita G. Hazell та Troels Skrydstrup. "Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of γ-amino acids employing carbohydrate-based chiral auxiliaries". Chem. Commun., № 17 (2004): 1962–63. http://dx.doi.org/10.1039/b405141f.

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34

Hashimoto, Takuya, Masato Omote, Yoshio Hato, Taichi Kano та Keiji Maruoka. "Asymmetric 1,3-Dipolar Cycloadditions ofN-Benzyl andN-Diphenylmethyl Nitrones and α,β-Unsaturated Aldehydes Catalyzed by Bis-Titanium Chiral Lewis Acids". Chemistry - An Asian Journal 3, № 2 (2008): 407–12. http://dx.doi.org/10.1002/asia.200700344.

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35

Katagiri, Nobuya, Makoto Okada, Chikara Kaneko, and Toshio Furuya. "Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids." Tetrahedron Letters 37, no. 11 (1996): 1801–4. http://dx.doi.org/10.1016/0040-4039(96)00122-0.

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36

Shindo, Mitsuru, Keiko Ohtsuki та Kozo Shishido. "Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with a chiral nitrone derived from l-serine leading to β-amino acid derivatives". Tetrahedron: Asymmetry 16, № 16 (2005): 2821–31. http://dx.doi.org/10.1016/j.tetasy.2005.07.023.

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37

DONDONI, A., F. JUNQUERA, F. L. MERCHAN, P. MERINO та T. TEJERO. "ChemInform Abstract: Addition of 2-Lithiofuran to Chiral α-Alkoxy Nitrones: A Stereoselective Approach to α-Epimeric β-Alkoxy-α- amino Acids." ChemInform 26, № 29 (2010): no. http://dx.doi.org/10.1002/chin.199529264.

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38

Murahashi, Shun-Ichi, Yasushi Imada, Toru Kawakami, Kazuhito Harada, Yoshiharu Yonemushi та Naomi Tomita. "ChemInform Abstract: Enantioselective Addition of Ketene Silyl Acetals to Nitrones Catalyzed by Chiral Titanium Complexes. Synthesis of Optically Active β-Amino Acids." ChemInform 33, № 31 (2010): no. http://dx.doi.org/10.1002/chin.200231095.

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39

Kiguchi, Toshiko, Mitsuko Shirakawa, Rina Honda, Ichiya Ninomiya, and Takeaki Naito. "ChemInform Abstract: Total Syntheses of (+)-Azimic Acid (VIII), (+)-Julifloridine (XV), and Proposed Structure of N-Methyljulifloridine via Cycloaddition of Nitrone to a Chiral Dipolarophile." ChemInform 30, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199918202.

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40

KATAGIRI, N., M. OKADA, C. KANEKO, and T. FURUYA. "ChemInform Abstract: Synthesis of Chiral Cyclic Nitrones via a Nitrosoketene Intermediate and Their Use for the Complete EPC Synthesis of Nonproteinogenic Amino Acids." ChemInform 27, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199626239.

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41

MERINO, P., S. FRANCO, F. L. MERCHAN та T. TEJERO. "ChemInform Abstract: Asymmetric Addition Reactions of Lithium (Trimethylsilyl)acetylide with Chiral α-Amino Nitrones. Synthesis of Diastereomerically Pure N-Hydroxy-α-amino Acids." ChemInform 30, № 1 (2010): no. http://dx.doi.org/10.1002/chin.199901078.

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42

Katagiri, Nobuya, Makoto Okada, Yoshihiro Morishita, and Chikara Kaneko. "Synthesis of chiral spiro 3-oxazolin-5-one 3-oxides (chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1,3-dipolar cycloaddition reactions leading to the EPC synthesis of modified amino acids." Tetrahedron 53, no. 16 (1997): 5725–46. http://dx.doi.org/10.1016/s0040-4020(97)00284-6.

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43

Ohtake, Hiroaki, Yasushi Imada та Shun-Ichi Murahashi. "Highly Diastereoselective Addition of a Chiral Ketene Silyl Acetal to Nitrones: Asymmetric Synthesis of β-Amino Acids and Key Intermediates of β-Lactam Antibiotics". Journal of Organic Chemistry 64, № 11 (1999): 3790–91. http://dx.doi.org/10.1021/jo9902291.

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44

KATAGIRI, N., M. OKADA, Y. MORISHITA, and C. KANEKO. "ChemInform Abstract: Synthesis of Chiral Spiro 3-Oxazolin-5-one 3-Oxides (Chiral Nitrones) via a Nitrosoketene Intermediate and Their Asymmetric 1,3-Dipolar Cycloaddition Reactions Leading to the EPC Synthesis of Modified Amino Acids." ChemInform 28, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199735141.

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45

Portolés, Raul, Juan Murga, Eva Falomir, Miguel Carda, Santiago Uriel та J. Alberto Marco. "Synthesis of α,α-Disubstituted α-Amino Acid Derivatives in Enantiopure Form via Stereoselective Addition of Grignard Reagents to a Chiral Acyclic Nitrone Derived from L-Erythrulose". Synlett 2002, № 05 (2002): 0711–14. http://dx.doi.org/10.1055/s-2002-25358.

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46

Ohtake, Hiroaki, Yasushi Imada та Shun-Ichi Murahashi. "ChemInform Abstract: Highly Diastereoselective Addition of a Chiral Ketene Silyl Acetal to Nitrones: Asymmetric Synthesis of β-Amino Acids and Key Intermediates of β-Lactam Antibiotics." ChemInform 30, № 39 (2010): no. http://dx.doi.org/10.1002/chin.199939167.

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47

Portoles, Raul, Juan Murga, Eva Falomir, Miguel Carda, Santiago Uriel та J. Alberto Marco. "ChemInform Abstract: Synthesis of α,α-Disubstituted α-Amino Acid Derivatives in Enantiopure Form via Stereoselective Addition of Grignard Reagents to a Chiral Acyclic Nitrone Derived from L-Erythrulose." ChemInform 33, № 36 (2010): no. http://dx.doi.org/10.1002/chin.200236192.

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48

Kawakami, Toru, Hiroaki Ohtake, Hiroaki Arakawa, Takahiro Okachi, Yasushi Imada та Shun-Ichi Murahashi. "ChemInform Abstract: Reversal of Diastereoselectivity of the Reaction of Chiral Boron and Titanium Enolates with Nitrones via N-Acyloxyiminium Intermediates. Asymmetric Synthesis of Diastereomeric α-Substituted β-Amino Acids." ChemInform 31, № 1 (2010): no. http://dx.doi.org/10.1002/chin.200001204.

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49

Aouadi, Kaïss, Moncef Msaddek, and Jean-Pierre Praly. "Cycloaddition of a chiral nitrone to allylic motifs: an access to enantiopure sugar-based amino acids displaying a stable glycosidic bond and to 4(S)-4-hydroxy-l-ornithine." Tetrahedron 68, no. 6 (2012): 1762–68. http://dx.doi.org/10.1016/j.tet.2011.12.048.

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50

Adhreai, Arwa AL, Mohammed ALSaeedy, Mazahar Farooqui, Ali Alrabie, Inas Al-Qadsy, and Usama Al-Timari. "Stereoselective Synthesis of Novel Chiral Open-Chain D-Ribose and D-Glucose- Derived Nitrones through 1,3-Dipolar Cycloaddition of Maleimide and Maleic Acid and Investigation of Their Antimicrobial Activity Via Molecular Docking and ADMET Studies." Journal of Molecular Structure 1256 (May 2022): 132481. http://dx.doi.org/10.1016/j.molstruc.2022.132481.

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