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Journal articles on the topic 'Oxazolines chirales'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 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

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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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

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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5

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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6

Alonso, P. J., J. I. Martínez, J. I. García, et al. "Caracterización, mediante espectroscopia EPR, de los catalizadores quirales bis (Oxazolina)-Cu soportados en Laponitas." Boletín de la Sociedad Española de Cerámica y Vidrio 39, no. 4 (2000): 552–55. http://dx.doi.org/10.3989/cyv.2000.v39.i4.817.

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7

Singh a, R. P. "Complexes of TiX4(X = Cl, OCHMe2) NEt2) withC2-ChiralBIS-Oxazolines." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 27, no. 1 (1997): 155–66. http://dx.doi.org/10.1080/00945719708000190.

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8

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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9

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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10

Herbert, Simon A., Laura J. van Laeren, Dominic C. Castell, and Gareth E. Arnott. "Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space." Beilstein Journal of Organic Chemistry 10 (November 25, 2014): 2751–55. http://dx.doi.org/10.3762/bjoc.10.291.

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The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji–Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds.

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11

Ollevier, Thierry. "Iron bis(oxazoline) complexes in asymmetric catalysis." Catalysis Science & Technology 6, no. 1 (2016): 41–48. http://dx.doi.org/10.1039/c5cy01357g.

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Asymmetric reactions catalyzed by iron complexes have attracted considerable attention because iron is a ubiquitous, inexpensive, and environmentally benign metal. This overview charts the development and application of chiral iron bis(oxazoline) and pyridine-2,6-bis(oxazoline) catalysts through their most prominent and innovative uses in asymmetric catalysis, especially in Lewis acid and oxidation catalysis.

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12

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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13

Zuo, Ziqing, Lei Zhang, Xuebing Leng, and Zheng Huang. "Iron-catalyzed asymmetric hydrosilylation of ketones." Chemical Communications 51, no. 24 (2015): 5073–76. http://dx.doi.org/10.1039/c5cc00612k.

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14

Yu, Feng, Pinhong Chen, and Guosheng Liu. "Pd(ii)-catalyzed intermolecular enantioselective hydroamination of styrenes." Organic Chemistry Frontiers 2, no. 7 (2015): 819–22. http://dx.doi.org/10.1039/c5qo00096c.

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15

Chen, Jianhui, Tuo Xi, and Zhan Lu. "10 gram-scale synthesis of a chiral oxazoline iminopyridine ligand and its applications." Organic Chemistry Frontiers 5, no. 2 (2018): 247–53. http://dx.doi.org/10.1039/c7qo00816c.

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16

Kumar, Dheeraj, Jatinder Singh, and Anil J. Elias. "Chiral multidentate oxazoline ligands based on cyclophosphazene cores: synthesis, characterization and complexation studies." Dalton Trans. 43, no. 37 (2014): 13899–912. http://dx.doi.org/10.1039/c4dt01741b.

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Chiral oxazoline derivatives of cyclophosphazenes were prepared and their complexation and catalytic studies for the asymmetric rearrangement of trichloroacetimidates to trichloroacetamides have been performed.

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17

Singh, Pradeep K., and Vinod K. Singh. "Chiral 2,6-bis(5',5'-diphenyloxazoline)pyridine as an efficient ligand for asymmetric catalysis." Pure and Applied Chemistry 84, no. 7 (2012): 1651–57. http://dx.doi.org/10.1351/pac-con-11-10-16.

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A modified tridentate pyridine bisoxazoline (pybox) ligand, possessing gem-diphenyl substitution at C-5 of the oxazoline rings, has been proved to be a very efficient ligand for enantioselective allylic oxidation, one-pot three-component synthesis of propargy-amines, and Friedel–Crafts alkylation of various aromatic compounds. We have shown that a 5',5'-diphenyl grouping in the oxazoline rings of chiral ligands is crucial for higher reaction rates as well as enhanced enantioselectivity.

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18

Angulo, Beatriz, José I. García, Clara I. Herrerías, José A. Mayoral, and Ana C. Miñana. "Polytopic bis(oxazoline)-based ligands for recoverable catalytic systems applied to the enantioselective Henry reaction." Organic & Biomolecular Chemistry 13, no. 35 (2015): 9314–22. http://dx.doi.org/10.1039/c5ob01033k.

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19

Ren, Li, Austin C. Chen, Andreas Decken, and Cathleen M. Crudden. "Chiral bidentate N-heterocyclic carbene complexes of Rh and Pd." Canadian Journal of Chemistry 82, no. 12 (2004): 1781–87. http://dx.doi.org/10.1139/v04-165.

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The synthesis of a new chiral, bidentate oxazoline/imidazolidene carbene precursor is described. This species is reacted with various metal salts in the presence of a base to generate rhodium and palladium complexes, which are characterized spectroscopically and crystallographically.Key words: chiral N-heterocyclic carbene, rhodium, palladium, oxazolidine, asymmetric catalysis.

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20

Meng, Ke, Jingzhao Xia, Yanzhao Wang, Xinghua Zhang, Guoqiang Yang, and Wanbin Zhang. "Ir/BiphPHOX-catalyzed asymmetric hydrogenation of 3-substituted 2,5-dihydropyrroles and 2,5-dihydrothiophene 1,1-dioxides." Organic Chemistry Frontiers 4, no. 8 (2017): 1601–5. http://dx.doi.org/10.1039/c7qo00248c.

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An efficient asymmetric hydrogenation of 3-substituted 2,5-dihydropyrroles and 2,5-dihydrothiophene 1,1-dioxides was developed using an Ir catalyst with an axially flexible chiral phosphine-oxazoline ligand.

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21

Pan, Yu, Wenqiang Li, Ning-Ning Wei, et al. "Highly active rare-earth metal catalysts for heteroselective ring-opening polymerization of racemic lactide." Dalton Transactions 48, no. 25 (2019): 9079–88. http://dx.doi.org/10.1039/c9dt00541b.

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22

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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23

Torres-Werlé, Maria, Adela Nano, Aline Maisse-François, and Stéphane Bellemin-Laponnaz. "Asymmetric benzoylation and Henry reaction using reusable polytopic bis(oxazoline) ligands and copper(ii)." New J. Chem. 38, no. 10 (2014): 4748–53. http://dx.doi.org/10.1039/c4nj00653d.

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Multitopic bis(oxazoline)-based chiral ligands are associated with copper to generate catalysts for the asymmetric benzoylation of meso-hydrobenzoin, the kinetic resolution of rac-hydrobenzoin and the asymmetric Henry reaction.

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24

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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25

Cao, Jing, Wanghui Yan, and Yiling Huang. "Design, synthesis and fluorescence behavior of novel chemosensor with a thieno[2,3-b]thiophene fluorophore." RSC Advances 6, no. 103 (2016): 101313–17. http://dx.doi.org/10.1039/c6ra19610a.

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A novel chemosensor with a thieno[2,3-b] thiophene fluorophore bearing an oxazoline receptor exhibited good selectivity to the dichromate anion, and also shows enantioselectivity for mandelic acid with a chiral receptor.

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26

Wang, Feijun, Shengke Li, Mingliang Qu, Mei-Xin Zhao, Lian-Jun Liu, and Min Shi. "Synthesis of axially chiral oxazoline–carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe2." Beilstein Journal of Organic Chemistry 8 (May 11, 2012): 726–31. http://dx.doi.org/10.3762/bjoc.8.81.

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Axially chiral oxazoline–carbene ligands with an N-naphthyl framework were successfully prepared, and their coordination behavior with AuCl·SMe2 was also investigated, affording the corresponding Au(I) complexes in moderate to high yields.

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27

Llewellyn, David B., and Bruce A. Arndtsen. "The use of a chiral borate counteranion as a 1H NMR shift reagent for cationic copper(I) complexes." Canadian Journal of Chemistry 81, no. 11 (2003): 1280–84. http://dx.doi.org/10.1139/v03-141.

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The chiral borate counteranion bis[(R)-1,1′-bi-2-naphtholato]borate (1) has been found to be a competent chiral 1H NMR shift reagent for cationic copper(I) complexes. This has been demonstrated by the addition of the Cu(NCMe)4+ salt of 1 to two classes of common chiral ligands in asymmetric catalysis: 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl (tol-BINAP) (2) and 2,2′-isopropylidenebis(4-phenyl-2-oxazoline) (3). In the case of ligand 2, the addition of 1 equiv. of either (R,R)-2 or (S,S)-2 to Cu(NCMe)4+1 results in well-resolved 1H NMR resonances for the two enantiomers. Examination of s

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28

Dodd, David W., Heather E. Toews, Michael J. Trevail, Michael C. Jennings, Robert HE Hudson, and Nathan D. Jones. "Synthesis and evaluation of the in vitro DNA-binding properties of chiral cis-dichloro(pyridyloxazoline)platinum(II) complexes." Canadian Journal of Chemistry 87, no. 1 (2009): 321–27. http://dx.doi.org/10.1139/v08-131.

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A series of chiral cis-dichloro(pyridyloxazoline)platinum(II) and palladium(II) complexes were synthesized and their reactivity towards a defined sequence of single-stranded and double-stranded DNA was investigated in comparison to cisplatin. The compounds differed in the nature and absolute configuration of the substituent at the C4 position of the oxazoline ring. The DNA-binding ability of these compounds was evaluated by HPLC analysis, post metal exposure, of enzymatic digests of an undecamer duplex containing one putative metallation site. Polyacrylamide gel electrophoresis (PAGE) and ther

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29

Hao, Xin-Qi, Cong Wang, Shuang-Liang Liu та ін. "Cobalt(ii)/(imidazoline–oxazoline)-catalyzed enantioselective Michael addition of 2-acetyl azaarenes to β-CF3-β-disubstituted nitroalkenes". Organic Chemistry Frontiers 4, № 2 (2017): 308–12. http://dx.doi.org/10.1039/c6qo00562d.

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Cobalt(ii)/(imidazoline–oxazoline)-catalyzed enantioselective Michael addition of 2-acetyl azaarenes to β-CF<sub>3</sub>-β-disubstituted nitroalkenes is reported, providing chiral compounds with an all-carbon quaternary stereocenter in high yields and excellent enantioselectivities.

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30

Goodrich, P., H. Q. Nimal Gunaratne, L. Hall, et al. "Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction." Dalton Transactions 46, no. 5 (2017): 1704–13. http://dx.doi.org/10.1039/c6dt04572c.

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A bis-oxazoline ligand has been complexed using Cu(ii) and Zn(ii) trifluoromethanesulfonate and a range of chiral ionic liquid (CIL) additives based on natural products were used as a co-catalyst for a Diels–Alder reaction.

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31

Berlan, J., та Y. Besace. "Addition d'organocuprates aux oxazolidines chirales α-β ethyleniques : II - Nature des Intermédiaires, mécanisme et stéréochimie". Tetrahedron 42, № 17 (1986): 4767–76. http://dx.doi.org/10.1016/s0040-4020(01)82057-3.

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32

Jagtap, Rahul A., Shidheshwar B. Ankade, Rajesh G. Gonnade, and Benudhar Punji. "Achiral and chiral NNN-pincer nickel complexes with oxazolinyl backbones: application in transfer hydrogenation of ketones." New Journal of Chemistry 45, no. 27 (2021): 11927–36. http://dx.doi.org/10.1039/d1nj01698a.

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33

Chen, Jianhui, Tuo Xi, Xiang Ren, Biao Cheng, Jun Guo, and Zhan Lu. "Asymmetric cobalt catalysts for hydroboration of 1,1-disubstituted alkenes." Org. Chem. Front. 1, no. 11 (2014): 1306–9. http://dx.doi.org/10.1039/c4qo00295d.

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Chiral iminopyridine oxazoline (IPO) ligands were designed, synthesized and utilized for the first cobalt-catalyzed highly regio- and enantioselective anti-Markovnikov hydroboration of 1,1-disubstituted aryl alkenes. These novel IPO ligands will likely be of high value for asymmetric transformations with first-row transition metals.

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34

Beletskaya, Irina, and Victor Desyatkin. "Asymmetric Friedel–Crafts/Michael Reaction of Indoles and Pyrroles with Coumarin-3-carbonylates." Synthesis 49, no. 18 (2017): 4327–34. http://dx.doi.org/10.1055/s-0036-1589024.

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Asymmetric Friedel–Crafts reactions of indoles or pyrroles with coumarin-3-carboxylates catalyzed by Cu(OTf)2 complexes with chiral bis(oxazoline) ligands have been developed. The highest ee (up to 82%) was achieved for indole with a nitro derivative of coumarin-3-carboxylate.

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35

Decken, Andreas, Robert A. Gossage, and Paras N. Yadav. "Oxazoline chemistry. Part VIII. Synthesis and characterization of a new class of pincer ligands derived from the 2-(o-anilinyl)-2-oxazoline skeleton Applications to the synthesis of group X transition metal catalysts." Canadian Journal of Chemistry 83, no. 8 (2005): 1185–89. http://dx.doi.org/10.1139/v05-163.

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The synthesis and characterization of a new and readily synthesized class of potentially anionic pincer ligands with C1 point group symmetries is described. These materials can be made via amide coupling of a 2-(2′-anilinyl)-2-oxazoline unit with picolinic acid; the incorporation of enantiopure oxazoline fragments facilitates the construction of chiral C1 pincers. Treatment of the free ligands with Pd metal sources leads to the formation of amidoPd pincer complexes in good yield. One of these Pd complexes has been characterized by single crystal X-ray diffraction methods, which confirms the p

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36

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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37

Peng, Jiahuan, and Da-Ming Du. "Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans." Beilstein Journal of Organic Chemistry 9 (June 24, 2013): 1210–16. http://dx.doi.org/10.3762/bjoc.9.137.

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The enantioselective tandem Friedel–Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).

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38

Berlan, J., Y. Besace, G. Pourcelot та P. Cresson. "Addition d'organocuprates aux oxazolidines chirales α-β ethyleniques : I - resultats - effets de sel et de solvant". Tetrahedron 42, № 17 (1986): 4757–65. http://dx.doi.org/10.1016/s0040-4020(01)82056-1.

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39

Kraft, Jochen, Martin Golkowski, and Thomas Ziegler. "Spiro-fused carbohydrate oxazoline ligands: Synthesis and application as enantio-discrimination agents in asymmetric allylic alkylation." Beilstein Journal of Organic Chemistry 12 (January 29, 2016): 166–71. http://dx.doi.org/10.3762/bjoc.12.18.

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In the present work, we describe a convenient synthesis of spiro-fused D-fructo- and D-psico-configurated oxazoline ligands and their application in asymmetric catalysis. The ligands were synthesized from readily available 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose and 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-psicopyranose, respectively. The latter compounds were partially deprotected under acidic conditions followed by condensation with thiocyanic acid to give an anomeric mixture of the corresponding 1,3-oxazolidine-2-thiones. The anomeric 1,3-oxazolidine-2-thiones were sep

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40

Wolińska, Ewa, Waldemar Wysocki, Danuta Branowska, and Zbigniew Karczmarzyk. "Synthesis and structures of three new pyridine-containing oxazoline ligands of complexes for asymmetric catalysis." Acta Crystallographica Section C Structural Chemistry 77, no. 9 (2021): 529–36. http://dx.doi.org/10.1107/s2053229621008202.

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Three new chiral pyridine-containing oxazoline derivatives with fluorine and perfluoromethyl groups, namely, 2-({2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C21H16F3N3O, 2-({5-fluoro-2-[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C18H17F4N3O, and 2-({2-[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C22H16F3N3O, as chiral ligands in metal-catalysed asymmetric reactions, were synthesized and characterized by spectral and X-ray diffraction methods. The conformat

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41

Taghvaee, Mahroo, and Robert A. Gossage. "Coordination chemistry and applications of metal phenolates containing an oxazoline group." Reviews in Inorganic Chemistry 33, no. 2-3 (2013): 119–28. http://dx.doi.org/10.1515/revic-2013-0004.

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AbstractThis review details the coordination chemistry aspects, applications, and catalytic relevance of materials containing a phenol unit appended to an oxazoline ring. The latter functionality can be chiral or achiral in nature. The binding motifs and catalytic potency of these materials in carbon-carbon bond forming processes and related reactions are compared and contrasted.

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42

Wrzeszcz, Zuzanna, and Renata Siedlecka. "Heteroaromatic N-Oxides Modified with a Chiral Oxazoline Moiety, Synthesis and Catalytic Applications." Catalysts 11, no. 4 (2021): 444. http://dx.doi.org/10.3390/catal11040444.

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Interesting properties of N-oxides and pyridine oxazoline compounds have become the starting point to synthesize compounds connecting both groups. A multi-step synthesis of a series of chiral oxazoline substituted pyridine N-oxides, alkyl derived of pyridine N-oxides, bipyridine N-oxides, and isoquinoline N-oxides, based on amino alcohols derived from natural amino acids or other previously prepared, is presented herein. Various synthetic pathways have been designed and tested according to the properties and limitations imposed by the target products. The encountered problems related to the st

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43

Jalba, Angela, Guillaume Levitre, Hoda Keipour, Samuel Lauzon, and Thierry Ollevier. "New chiral bis(oxazolinyl)bipyridine ligands and application in the iron catalyzed asymmetric hydrosilylation of ketones." French-Ukrainian Journal of Chemistry 3, no. 2 (2015): 44–53. http://dx.doi.org/10.17721/fujcv3i2p44-53.

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C2 symmetrical 6,6′-bis(oxazolinyl)-2,2′-bipyridine (bipybox) chiral ligands have been synthesized from readily available 2,2′-bipyridine. Catalytic asymmetric hydrosilylation of ketones was studied using this family of ligands in the presence of iron(II) acetate.

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44

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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45

Katritzky, Alan R., Justo Cobo-Domingo, Baozhen Yang, and Peter J. Steel. "Diastereoselective Synthesis of N-Substituted Ethyl 4-Phenyloxazolidine-2-carboxylates." Journal of Chemical Research 23, no. 2 (1999): 162–63. http://dx.doi.org/10.1177/174751989902300248.

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( S)-2-Phenylglycinol, ethyl glyoxylate, formaldehyde and benzotriazole formed stereospecifically ethyl (2 S,4 S)- N-(benzotriazol-1-yl)methyl-4-phenyloxazolidine-2-carboxylate (1) which was converted into chiral N-substituted oxazolidines, via regiospecific substitutions of the benzotriazolyl residue.

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46

Gable, RW, RL Martin, and MA Rizzacasa. "A Synthetic Approach to (+)-Dioncophylline C." Australian Journal of Chemistry 48, no. 12 (1995): 2013. http://dx.doi.org/10.1071/ch9952013.

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In a synthetic approach to (+)-dioncophylline C (1), a coupling between the chiral oxazoline (3) and the Grignard reagent obtained from bromide (4) gave the major biaryl (5) and the minor biaryl (12) in good yield and high diastereoselectivity (yield 70%; ratio 91:9). The stereochemistry of the major biaryl (5) was confirmed by X-ray structure analysis of the derived crystalline iodide salt (13).

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47

Rubina, Marina, William M. Sherrill, Alexey Yu Barkov, and Michael Rubin. "Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction." Beilstein Journal of Organic Chemistry 10 (July 7, 2014): 1536–48. http://dx.doi.org/10.3762/bjoc.10.158.

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A novel class of chiral phosphanyl-oxazoline (PHOX) ligands with a conformationally rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities and significantly suppressing product isomerization. Factors affecting the selectivity and the rate of the

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Mehta, Meera, Timothy C. Johnstone, Jolie Lam, et al. "Synthesis and oxidation of phosphine cations." Dalton Trans. 46, no. 41 (2017): 14149–57. http://dx.doi.org/10.1039/c7dt03175k.

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Cationic phosphines of the form [(L)PPh<sub>2</sub>]<sup>+</sup> are prepared from Ph<sub>2</sub>PCl and carbenes (L), including a chiral bis(oxazoline)-based carbene, a cyclic(alkyl)(amino) carbene, and a 1,2,3-triazolium-derived carbene. A related dication was prepared from PhPCl<sub>2</sub> and a bis-carbene. The monocations, but not the dication, can be oxidized with XeF<sub>2</sub>.

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Brunner, Henri, Matthias Weber, and Manfred Zabel. "Asymmetric Catalysis, 154 [1]. New 1,1’-Binaphthyl Ligands for Enantioselective Catalysis." Zeitschrift für Naturforschung B 58, no. 9 (2003): 821–26. http://dx.doi.org/10.1515/znb-2003-0902.

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Chiral binaphthyl compounds, especially those with different substituents in 2- and 2’-position of the binaphthyl system, have gained interest as constituents of successful ligands in various catalytic reactions. Here, we present the synthesis and characterization of new binaphthyl ligands containing oxazoline, cyano and amide substituents in 2’-position in addition to methoxy, hydroxy or amino groups in 2-position. Starting from these compounds new ligands for enantioselective catalysis will be accessible.

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Lloyd-Jones, Guy C., and Andreas Pfaltz. "Synthesis and Structures of Low-Valent Tungsten Complexes Bearing Chiral Oxazoline-Derived Ligands." Zeitschrift für Naturforschung B 50, no. 3 (1995): 361–67. http://dx.doi.org/10.1515/znb-1995-0309.

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The synthesis of low-valent tungsten (0 and II) complexes bearing chiral bidentate phosphino- oxazoline or bisoxazoline ligands is described. The structures of four of the complexes have been determined by single crystal X-ray analyses. Tungsten(II)-allyl complexes of the type [W(CO)2(PN)(C3H5)Cl] (PN = phosphino-oxazoline) are fluxional in solution, but can be crystallized as single diastereoisomers. The complex [W(CO)3(PN)(CH3CN)], which also crystallizes as a single diastereoisomer, is readily oxidized in solution and solid state, in stark contrast to analogous compounds bearing four carbon

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