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Journal articles on the topic 'Chiral oxazolines'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Huang, Xin, Weizhao Zhao, De-Li Chen, et al. "Benzyne-mediated trichloromethylation of chiral oxazolines." Chemical Communications 55, no. 14 (2019): 2070–73. http://dx.doi.org/10.1039/c9cc00557a.

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2

Puts, Rutger D., Jade Chao, and Dotsevi Y. Sogah. "Novel Chiral Biaryl Bis(oxazolines)." Synthesis 1997, no. 04 (1997): 431–38. http://dx.doi.org/10.1055/s-1997-1213.

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3

Qin, Tian, Quanbin Jiang, Jieying Ji, Jie Luo, and Xiaodan Zhao. "Chiral selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated 2,5-disubstituted oxazolines." Organic & Biomolecular Chemistry 17, no. 7 (2019): 1763–66. http://dx.doi.org/10.1039/c8ob02575d.

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Chiral selenide-catalyzed enantioselective trifluoromethylthiolation of 1,1-disubstituted alkenes is disclosed. Various chiral trifluoromethylthiolated 2,5-disubstituted oxazolines were obtained in good yields with high enantioselectivities.

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4

Le Bail, Marc, David J. Aitken, Fabrice Vergne, and Henri-Philippe Husson. "Alkylation of chiral 2-(aminomethyl)oxazolines." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1997): 1681–90. http://dx.doi.org/10.1039/a608030h.

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5

Xi, Tuo, Yuncai Mei, and Zhan Lu. "Palladium-Catalyzed C-2 C–H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands." Organic Letters 17, no. 24 (2015): 5939–41. http://dx.doi.org/10.1021/acs.orglett.5b03041.

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6

Zhou, Xin, Baiyi Mao, and Zhanbin Zhang. "Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines." Molecules 26, no. 4 (2021): 857. http://dx.doi.org/10.3390/molecules26040857.

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Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)2 was found to be the most effective.

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7

Martínez-Pardo, Pablo, Gonzalo Blay, M. Carmen Muñoz, José R. Pedro, Amparo Sanz-Marco, and Carlos Vila. "Enantioselective synthesis of chiral oxazolines from unactivated ketones and isocyanoacetate esters by synergistic silver/organocatalysis." Chemical Communications 54, no. 23 (2018): 2862–65. http://dx.doi.org/10.1039/c8cc00856f.

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Synergistic catalysis by Ag<sup>+</sup> and bifunctional squaramide allows the highly diastereo- and enantioselective reaction of isocyanoacetate esters and ketones to give chiral oxazolines bearing a quaternary stereocenter.

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8

Mamaghani, M., N. O. Mahmoodi, and S. Fallah Ghasemi. "An efficient synthesis of New chiral oxazolines." Journal of the Iranian Chemical Society 7, no. 4 (2010): 972–77. http://dx.doi.org/10.1007/bf03246093.

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9

Mulahmetovic, Ensar, and Gráinne C. Hargaden. "Synthetic Routes to Oxazolines." Mini-Reviews in Organic Chemistry 16, no. 6 (2019): 507–26. http://dx.doi.org/10.2174/1570193x15666180802105505.

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In this mini-review, the main synthetic routes used in the preparation of oxazolines is presented. The review is systematically carried out and the syntheses are presented in terms of precursors utilised (nitriles, aldehydes and carboxylic acids). Additionally, the reported synthesis of all chiral and achiral oxazolines involve either the use of amino alcohols as essential building blocks or some form of intramolecular cyclisation reactions. A comparison of the effectiveness of various reaction initiators such as Lewis acids, bases, oxidants and metals as well as their respective reaction cond

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10

Kim, Sung-Gon, Sunderraman Sambasivan та Kyo-Han Ahn. "Chiral Discrimination of α-Chiral Ammonium Ions by Sterically Geared Chiral Tripodal Oxazolines". Bulletin of the Korean Chemical Society 31, № 3 (2010): 724–26. http://dx.doi.org/10.5012/bkcs.2010.31.03.724.

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11

Brunner, Henri, and Bernd Haßler. "Enantioselective Catalysis, 120 [1] New Optically Active Pyrrole-oxazolines." Zeitschrift für Naturforschung B 53, no. 4 (1998): 476–80. http://dx.doi.org/10.1515/znb-1998-0414.

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Abstract 14 new optically active pyrrole-oxazolines were synthesised from 2-pyrrole-carbonitrile or methyl 2-pyrrole-carboximidate and chiral amino alcohols. Their use in copper-catalysed enantioselective cyclopropanation reactions gave only low optical yields (3-14%ee).

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12

Chen, Jiean, Yong Huang та Fei Wang. "Synthesis of Optically Active Oxazolines by an Organocatalytic Isocyanoacetate Aldol Reaction with α-Keto Esters". Synlett 28, № 11 (2017): 1300–1304. http://dx.doi.org/10.1055/s-0036-1588718.

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An enantioselective [3+2] cyclization is reported for the construction of a chiral oxazoline skeleton in moderate yield and up to 97% ee. The reactivity and stereochemical discrimination originate from the noncovalent interaction and orientation of a bifunctional catalyst. The novel combination of an α-keto ester and an α-isocyanoacetate establishes an oxazoline which could be a potential chiral ligand for metal-mediated catalysis, and also could be easily converted into an optically active β-hydroxy-α-amino acid.

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13

Nakamura, Kento, Masaru Kondo, Chandu G. Krishnan, Shinobu Takizawa, and Hiroaki Sasai. "Azopyridine-based chiral oxazolines with rare-earth metals for photoswitchable catalysis." Chemical Communications 57, no. 60 (2021): 7414–17. http://dx.doi.org/10.1039/d1cc02602j.

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An azopyridine-based oxazoline ligand was developed as a chiral photoswitchable ligand. The ligand coordinated to rare-earth metal modulated the enantioselectivity of cyclic aminal forming reaction by photoisomerization.

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14

Meyers, A. I., and Giulia Licini. "Intramolecular asymmetric tandem additions to chiral naphthyl oxazolines." Tetrahedron Letters 30, no. 31 (1989): 4049–52. http://dx.doi.org/10.1016/s0040-4039(00)99318-3.

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15

Lu, Peng, Chong-Lei Ji, and Zhan Lu. "Nickel-Catalyzed C−H Heteroarylation of Chiral Oxazolines." Asian Journal of Organic Chemistry 7, no. 3 (2017): 542–44. http://dx.doi.org/10.1002/ajoc.201700446.

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16

LE BAIL, M., D. J. AITKEN, F. VERGNE, and H. P. HUSSON. "ChemInform Abstract: Alkylation of Chiral 2-(Aminomethyl)oxazolines." ChemInform 28, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199743072.

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17

Kim, Sung-Gon, Hye Ran Seong, Jeongryul Kim, and Kyo Han Ahn. "Synthesis of C1-symmetric chiral tripodal oxazolines through an oxazoline exchange reaction with amino alcohols." Tetrahedron Letters 45, no. 37 (2004): 6835–38. http://dx.doi.org/10.1016/j.tetlet.2004.07.107.

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18

Minakata, Satoshi, Masaaki Nishimura, Toru Takahashi, Yoji Oderaotoshi, and Mitsuo Komatsu. "Direct asymmetric synthesis of oxazolines from olefins using a chiral nitridomanganese complex: a novel three-component coupling leading to chiral oxazolines." Tetrahedron Letters 42, no. 51 (2001): 9019–22. http://dx.doi.org/10.1016/s0040-4039(01)01963-3.

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19

Štěpnička, Petr, Tomáš Baše, Ivana Císařová, Jiří Kubišta, Štěpán Vyskočil, and Martin Štícha. "Synthesis and Catalytic Activity of Spaced Ferrocene Oxazolines." Collection of Czechoslovak Chemical Communications 68, no. 7 (2003): 1206–32. http://dx.doi.org/10.1135/cccc20031206.

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Chiral 2-[{N-aryl-N-(ferrocenylmethyl)amino}methyl]-4-(1-methylethyl)-4,5-dihydroxazoles with various substituents at the aryl ring were prepared by alkylation of N-(ferrocenylmethyl)anilines, FcCH2NHC6H4R (Fc = ferrocenyl), with (S)-2-(chloromethyl)-4-(1-methylethyl)-4,5-dihydrooxazole. The oxazoles, substituted anilines, and the precursors of the latter, the respective Schiff bases FcCH=NC6H4R, were characterized by standard methods and further studied by mass spectrometry. The oxazoles were further tested as chiral auxiliaries in the addition of diethylzinc to benzaldehyde but showed only n

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20

Yang, Guoqiang, and Wanbin Zhang. "Renaissance of pyridine-oxazolines as chiral ligands for asymmetric catalysis." Chemical Society Reviews 47, no. 5 (2018): 1783–810. http://dx.doi.org/10.1039/c7cs00615b.

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21

Tasic, Gordana, Radomir Matovic та Radomir Saicic. "Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach". Journal of the Serbian Chemical Society 69, № 11 (2004): 981–90. http://dx.doi.org/10.2298/jsc0411981t.

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A method for the stereoselective homologation of ?-amino acids into syn-?-hydroxy-?-amino acids is described, based on the conversion of stereoisomeric cyanohydrins into trans-oxazolines. The synthetic potential of the method is illustrated in the enantioselective formal synthesis of Bestatin.

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22

Toste, F. Dean, Arnab K. Chatterjee, and Robert H. Grubbs. "Functional group diversity by ruthenium-catalyzed olefin cross-metathesis." Pure and Applied Chemistry 74, no. 1 (2002): 7–10. http://dx.doi.org/10.1351/pac200274010007.

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Ruthenium-catalyzed olefin cross-metathesis tolerates a wide range of functional groups, including phosphine-boranes, sulfides, amines, phenols, and oxazolines. The high functional group tolerance allows for the use of an olefin as a linchpin for the synthesis of a variety of bi-, tri-, and tetradentate chiral ligands with a high degree of functional group diversity.

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23

Meyers, A. I., Wolfgang Schmidt, and Marc J. Mckennon. "Asymmetric Addition to Chiral Aromatic and Unsaturated Oxazolines Using a Novel Chiral Auxiliary." Synthesis 1993, no. 02 (1993): 250–62. http://dx.doi.org/10.1055/s-1993-25842.

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24

Kim, Jeongryul, Sung-Gon Kim, Hye Ran Seong, and Kyo Han Ahn. "Breaking theC3-Symmetry of Chiral Tripodal Oxazolines: Enantio-Discrimination of Chiral Organoammonium Ions." Journal of Organic Chemistry 70, no. 18 (2005): 7227–31. http://dx.doi.org/10.1021/jo050872p.

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25

González, Jaime, Diego Martínez-Otero, Bernardo A. Frontana-Uribe, and Erick Cuevas-Yañez. "Synthesis of chiral aza-bis(oxazolines) derived from (+)-camphor." Tetrahedron: Asymmetry 28, no. 4 (2017): 505–10. http://dx.doi.org/10.1016/j.tetasy.2017.03.001.

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26

Cevallos, Alexandre, Ramon Rios, Albert Moyano*, Miquel A. Pericàs, and Antoni Riera. "A convenient synthesis of chiral 2-alkynyl-1,3-oxazolines." Tetrahedron: Asymmetry 11, no. 21 (2000): 4407–16. http://dx.doi.org/10.1016/s0957-4166(00)00409-2.

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27

Sammakia, Tarek, and Eric L. Stangeland. "Transfer Hydrogenation with Ruthenium Complexes of Chiral (Phosphinoferrocenyl)oxazolines." Journal of Organic Chemistry 62, no. 18 (1997): 6104–5. http://dx.doi.org/10.1021/jo9711044.

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28

Wenzel, Marianne, and Eric Meggers. "Chiral (Mercaptophenyl)oxazolines as Auxiliaries for Asymmetric Coordination Chemistry." European Journal of Inorganic Chemistry 2012, no. 19 (2012): 3168–75. http://dx.doi.org/10.1002/ejic.201200203.

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29

REISER, O. "ChemInform Abstract: Oxazolines: Chiral Building Blocks, Auxiliaries and Ligands." ChemInform 27, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199645296.

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30

Glos, Martin, and Oliver Reiser. "ChemInform Abstract: Oxazolines: Chiral Building Blocks, Auxiliaries and Ligands." ChemInform 33, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.200217265.

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31

Glos, Martin, and Oliver Reiser. "Aza-bis(oxazolines): New Chiral Ligands for Asymmetric Catalysis†." Organic Letters 2, no. 14 (2000): 2045–48. http://dx.doi.org/10.1021/ol005947k.

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32

Desimoni, Giovanni, Giuseppe Faita, and Mariella Mella. "A stereodivergent synthesis of chiral 4,5-disubstituted bis(oxazolines)." Tetrahedron 52, no. 43 (1996): 13649–54. http://dx.doi.org/10.1016/0040-4020(96)00817-4.

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33

Minakata, Satoshi, Masaaki Nishimura, Toru Takahashi, Yoji Oderaotoshi, and Mitsuo Komatsu. "ChemInform Abstract: Direct Asymmetric Synthesis of Oxazolines from Olefins Using a Chiral Nitridomanganese Complex: A Novel Three-Component Coupling Leading to Chiral Oxazolines." ChemInform 33, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.200211109.

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34

Takayama, Tomoaki, Jun Nakazawa, and Shiro Hikichi. "A pseudotetrahedral nickel(II) complex with a tridentate oxazoline-based scorpionate ligand: chlorido[tris(4,4-dimethyloxazolin-2-yl)phenylborato]nickel(II)." Acta Crystallographica Section C Structural Chemistry 72, no. 11 (2016): 842–45. http://dx.doi.org/10.1107/s2053229616012183.

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Poly(pyrazol-1-yl)borates have been utilized extensively in coordination compounds due to their high affinity toward cationic metal ions on the basis of electrostatic interactions derived from the mononegatively charged boron centre. The original poly(pyrazol-1-yl)borates, christened `scorpionates', were pioneered by the late Professor Swiatoslaw Trofimenko and have expanded to include various borate ligands with N-, P-, O-, S-, Se- and C-donors. Scorpionate ligands with boron–carbon bonds, rather than the normal boron–nitrogen bonds, have been developed and in these new types of scorpionate l

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35

Boppisetti, Jagadish K., and Vladimir B. Birman. "Asymmetric Oxidation ofo-Alkylphenols with Chiral 2-(o-Iodoxyphenyl)-oxazolines." Organic Letters 11, no. 6 (2009): 1221–23. http://dx.doi.org/10.1021/ol8029092.

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36

Ella-Menye, Jean-Rene, and Guijun Wang. "Synthesis of chiral 2-oxazolidinones, 2-oxazolines, and their analogs." Tetrahedron 63, no. 40 (2007): 10034–41. http://dx.doi.org/10.1016/j.tet.2007.07.044.

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37

Rottmann, Antje, and J. Liebscher. "Chiral 2-(?-Aminoalkyl)-oxazolines by ring transformation of lactam derivatives." Journal f�r Praktische Chemie/Chemiker-Zeitung 338, no. 1 (1996): 397–402. http://dx.doi.org/10.1002/prac.19963380179.

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38

MEYERS, A. I., W. SCHMIDT, and M. J. MCKENNON. "ChemInform Abstract: Asymmetric Addition to Chiral Aromatic and Unsaturated Oxazolines Using a Novel Chiral Auxiliary." ChemInform 24, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199326054.

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39

Mézlová, Marie, Hana Petříčková, Petr Maloň, Václav Kozmík, and Jiří Svoboda. "Axially Chiral 3,3'-Bi(1-benzothiophene)-2,2'-dicarboxylic Acid and Its Derivatives." Collection of Czechoslovak Chemical Communications 68, no. 5 (2003): 1020–38. http://dx.doi.org/10.1135/cccc20031020.

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Ullmann dimerization of substituted methyl 3-X-1-benzothiophene-2-carboxylates 1-7 (X = Cl, Br) gave rise to the corresponding dimeric 3,3'-bi(1-benzothiophene) esters 8-13. Resolution of the title acid 20 by fractional crystallization of its mono- and bisquininium salt afforded pure (R)- and (S)-enantiomers, the optical purity and absolute configuration of which was confirmed by CD spectrometry and by X-ray crystallography. Ullmann dimerization of chiral oxazolines 23 and 24 derived from 2 proceeded without any diastereodifferentiation. Reduction of (R)- and (S)-20 afforded the corresponding

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40

Florio, Saverio, Vito Capriati, Renzo Luisi, and Alessandro Abbotto. "Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes." Tetrahedron Letters 40, no. 41 (1999): 7421–25. http://dx.doi.org/10.1016/s0040-4039(99)01480-x.

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41

Wu, Xin-Yan, Xiang-Hong Li, and Qi-Lin Zhou. "Chiral quinolinyl-oxazolines as ligands for copper(I)-catalyzed asymmetric cyclopropanation." Tetrahedron: Asymmetry 9, no. 23 (1998): 4143–50. http://dx.doi.org/10.1016/s0957-4166(98)00455-8.

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42

Wu, Xin-Yan, Yan-Yan Shen, Bing Ma, Qi-Lin Zhou, and Albert S. C. Chan. "Chiral pyridinyl-oxazolines as ligands for copper(I)-catalyzed asymmetric cyclopropanation." Journal of Molecular Catalysis A: Chemical 157, no. 1-2 (2000): 59–63. http://dx.doi.org/10.1016/s1381-1169(99)00442-2.

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43

Pouilhes, A., E. Uriarte, C. Kouklovsky та ін. "Chiral α,β-unsaturated oxazolines in the asymmetric diels-alder reaction". Tetrahedron Letters 30, № 11 (1989): 1395–98. http://dx.doi.org/10.1016/s0040-4039(00)99474-7.

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44

Gao, Ming Zhang, Bo Wang, Deyuan Kong, Ralph A. Zingaro, Abraham Clearfield, and Zun Le Xu. "Sulfur‐Containing Chiral Bis(oxazolines) Tested in Copper‐Catalyzed Asymmetric Cyclopropanation." Synthetic Communications 35, no. 20 (2005): 2665–73. http://dx.doi.org/10.1080/00397910500213948.

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45

Cevallos, Alexandre, Ramon Rios, Albert Moyano, Miquel A. Pericas, and Antoni Riera. "ChemInform Abstract: A Convenient Synthesis of Chiral 2-Alkynyl-1,3-oxazolines." ChemInform 32, no. 14 (2001): no. http://dx.doi.org/10.1002/chin.200114140.

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46

DESIMONI, G., G. FAITA, and M. MELLA. "ChemInform Abstract: A Stereodivergent Synthesis of Chiral 4,5-Disubstituted Bis(Oxazolines) ." ChemInform 28, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199707145.

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47

SAMMAKIA, T., and E. L. STANGELAND. "ChemInform Abstract: Transfer Hydrogenation with Ruthenium Complexes of Chiral (Phosphinoferrocenyl)oxazolines." ChemInform 29, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199801031.

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48

Leonard, William R., Jeffrey L. Romine, and A. I. Meyers. "A rapid and efficient synthesis of chiral 2-hydro-2-oxazolines." Journal of Organic Chemistry 56, no. 5 (1991): 1961–63. http://dx.doi.org/10.1021/jo00005a059.

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49

Glos, Martin, and Oliver Reiser. "ChemInform Abstract: Aza-bis(oxazolines): New Chiral Ligands for Asymmetric Catalysis." ChemInform 31, no. 43 (2000): no. http://dx.doi.org/10.1002/chin.200043029.

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50

Deng, Tao, and Chun Cai. "Fluorous chiral bis(oxazolines): Synthesis and application in asymmetric Henry reaction." Journal of Fluorine Chemistry 156 (December 2013): 183–86. http://dx.doi.org/10.1016/j.jfluchem.2013.09.014.

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