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1

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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2

Jones, Geraint, and Christopher J. Richards. "Simple phosphinite–oxazoline ligands for asymmetric catalysis." Tetrahedron Letters 42, no. 32 (2001): 5553–55. http://dx.doi.org/10.1016/s0040-4039(01)01041-3.

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3

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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4

Bakhtiari, Atefeh, and Javad Safaei-Ghomi. "Effects of Chiral Ligands on the Asymmetric Carbonyl-Ene Reaction." Synlett 30, no. 15 (2019): 1738–64. http://dx.doi.org/10.1055/s-0037-1611875.

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The carbonyl-ene reaction is one of the most well-known reactions for C–C bond formation. Based on frontier molecular orbitals (FMO), carbonyl-ene reactions occur between the highest occupied molecular orbital (HOMO) of the ene compound bearing an active hydrogen atom at the allylic center and the lowest unoccupied molecular orbital (LUMO) of the electron-deficient enophile, which is a carbonyl compound. A high activation barrier enforces the concerted ene reaction rather than a Diels–Alder reaction at high temperature. Employing a catalytic system can eliminate defects in the ene reaction, an
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5

Hanessian, Stephen, Eric Jnoff, Noemy Bernstein, and Michel Simard. "Bifunctional bis(oxazolines) as potential ligands in catalytic asymmetric reactions." Canadian Journal of Chemistry 82, no. 2 (2004): 306–13. http://dx.doi.org/10.1139/v03-198.

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C2-symmetrical bis(oxazoline) ligands bearing pendant alkylthio ether groups were synthesized, and the structures of Cu complexes were determined by single crystal X-ray diffraction. The potential utility in catalysis was shown in the asymmetric addition of methyllithium to an aromatic aldimine, which resulted in a mixture of products with an enantiomeric excess of 68%.Key words: two-center catalysis, bis(oxazoline), aldimine, imine alkylation.
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6

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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7

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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8

Padevět, Jaroslav, Marcus G. Schrems, Robin Scheil, and Andreas Pfaltz. "NeoPHOX – a structurally tunable ligand system for asymmetric catalysis." Beilstein Journal of Organic Chemistry 12 (June 13, 2016): 1185–95. http://dx.doi.org/10.3762/bjoc.12.114.

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A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central intermediate is a NeoPHOX derivative bearing a methoxycarbonyl group at the stereogenic center next to the oxazoline N atom. The addition of methylmagnesium chloride leads to a tertiary alcohol, which can be acylated or silylated to produce NeoPHOX ligands with different sterical demand. The new NeoPHOX ligands were tested in the iridium-catalyzed asymmetric hydrogenation and palladium-catalyzed allylic substitution. In both reactions high enantioselectivities were achieved, that were comparable
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9

Hoarau, O., H. Aït-Haddou, M. Castro, and G. G. A. Balavoine. "New homochiral bis(oxazoline) ligands for asymmetric catalysis." Tetrahedron: Asymmetry 8, no. 22 (1997): 3755–64. http://dx.doi.org/10.1016/s0957-4166(97)00499-0.

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10

Bronger, Raymond P. J., and Patrick J. Guiry. "Aminophosphine–oxazoline and phosphoramidite–oxazoline ligands and their application in asymmetric catalysis." Tetrahedron: Asymmetry 18, no. 9 (2007): 1094–102. http://dx.doi.org/10.1016/j.tetasy.2007.04.020.

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11

Biosca, Maria, Oscar Pàmies, and Montserrat Diéguez. "Ir–Biaryl phosphite–oxazoline catalyst libraries: a breakthrough in the asymmetric hydrogenation of challenging olefins." Catalysis Science & Technology 10, no. 3 (2020): 613–24. http://dx.doi.org/10.1039/c9cy02501d.

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12

Desimoni, Giovanni, Giuseppe Faita, and Karl Anker Jørgensen. "C2-Symmetric Chiral Bis(Oxazoline) Ligands in Asymmetric Catalysis." Chemical Reviews 106, no. 9 (2006): 3561–651. http://dx.doi.org/10.1021/cr0505324.

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13

Jönsson, Christina, Kristina Hallman, Helene Andersson, et al. "Immobilized oxazoline-containing Ligands in asymmetric catalysis—a review." Bioorganic & Medicinal Chemistry Letters 12, no. 14 (2002): 1857–61. http://dx.doi.org/10.1016/s0960-894x(02)00270-6.

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14

Hargaden, Gráinne C., and Patrick J. Guiry. "Recent Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis." Chemical Reviews 109, no. 6 (2009): 2505–50. http://dx.doi.org/10.1021/cr800400z.

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15

Jones, Geraint, and Christopher J. Richards. "ChemInform Abstract: Simple Phosphinite-Oxazoline Ligands for Asymmetric Catalysis." ChemInform 32, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.200145039.

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16

Gade, Lutz H., and Stéphane Bellemin-Laponnaz. "Mixed oxazoline-carbenes as stereodirecting ligands for asymmetric catalysis." Coordination Chemistry Reviews 251, no. 5-6 (2007): 718–25. http://dx.doi.org/10.1016/j.ccr.2006.05.015.

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17

HOARAU, O., H. AIT-HADDOU, M. CASTRO, and G. G. A. BALAVOINE. "ChemInform Abstract: New Homochiral Bis(oxazoline) Ligands for Asymmetric Catalysis." ChemInform 29, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199812036.

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18

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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19

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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20

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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21

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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22

Liu, Lei, Hongli Ma, Yanhua Wu, et al. "New Application Progress of Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis." Chinese Journal of Organic Chemistry 33, no. 11 (2013): 2283. http://dx.doi.org/10.6023/cjoc201306001.

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23

Desimoni, Giovanni, Giuseppe Faita, and Karl Anker Jørgensen. "Update 1 of:C2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis." Chemical Reviews 111, no. 11 (2011): PR284—PR437. http://dx.doi.org/10.1021/cr100339a.

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24

PFALTZ, A. "ChemInform Abstract: Chiral Semicorrin and Bis-oxazoline Ligands in Asymmetric Catalysis." ChemInform 27, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199636263.

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25

McKeon, Seán C., Helge Müller-Bunz, and Patrick J. Guiry. "Synthesis of Thiazoline-Oxazoline Ligands and Their Application in Asymmetric Catalysis." European Journal of Organic Chemistry 2011, no. 35 (2011): 7107–15. http://dx.doi.org/10.1002/ejoc.201101335.

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26

Joensson, Christina, Kristina Hallman, Helene Andersson, et al. "ChemInform Abstract: Immobilized Oxazoline-Containing Ligands in Asymmetric Catalysis - A Review." ChemInform 33, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.200248232.

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27

Connon, Robert, Brendan Roche, Balaji V. Rokade, and Patrick J. Guiry. "Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis." Chemical Reviews 121, no. 11 (2021): 6373–521. http://dx.doi.org/10.1021/acs.chemrev.0c00844.

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28

Wang, Qian, Zongpeng Zhang, Caiyou Chen та ін. "Iridium catalysts with modular axial-unfixed biphenyl phosphine–oxazoline ligands: asymmetric hydrogenation of α,β-unsaturated carboxylic acids". Organic Chemistry Frontiers 4, № 4 (2017): 627–30. http://dx.doi.org/10.1039/c6qo00677a.

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29

Wang, Qian, Zongpeng Zhang, Caiyou Chen та ін. "Correction: Iridium catalysts with modular axial-unfixed biphenyl phosphine–oxazoline ligands: asymmetric hydrogenation of α,β-unsaturated carboxylic acids". Organic Chemistry Frontiers 4, № 4 (2017): 631. http://dx.doi.org/10.1039/c7qo90009k.

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Correction for ‘Iridium catalysts with modular axial-unfixed biphenyl phosphine–oxazoline ligands: asymmetric hydrogenation of α,β-unsaturated carboxylic acids’ by Qian Wang et al., Org. Chem. Front., 2017, DOI: 10.1039/c6qo00677a.
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30

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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31

Qiu, Zhongxuan, Rui Sun, and Dawei Teng. "Synthesis of highly rigid phosphine–oxazoline ligands for palladium-catalyzed asymmetric allylic alkylation." Organic & Biomolecular Chemistry 16, no. 41 (2018): 7717–24. http://dx.doi.org/10.1039/c8ob02265h.

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32

McManus, Helen A., and Patrick J. Guiry. "Recent Developments in the Application of Oxazoline-Containing Ligands in Asymmetric Catalysis." Chemical Reviews 104, no. 9 (2004): 4151–202. http://dx.doi.org/10.1021/cr040642v.

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33

Wolf, Christian, and Hanhui Xu. "Asymmetric catalysis with chiral oxazolidine ligands." Chemical Communications 47, no. 12 (2011): 3339. http://dx.doi.org/10.1039/c0cc04629a.

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34

Ye, Xiang-Yu, Zhi-Qin Liang, Cong Jin, Qi-Wei Lang, Gen-Qiang Chen, and Xumu Zhang. "Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin via iridium-catalyzed asymmetric hydrogenation." Chemical Communications 57, no. 2 (2021): 195–98. http://dx.doi.org/10.1039/d0cc06311h.

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A series of highly rigid oxa-spiro phosphine–oxazoline ligands (O-SIPHOX) were synthesized efficiently, their iridium complexes showed high reactivity and enantioselectivity in the synthesis of key intermediate of anti-obesity drug lorcaserin.
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35

Imrich, Michael R., Jochen Kraft, Cäcilia Maichle-Mössmer, and Thomas Ziegler. "D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation." Beilstein Journal of Organic Chemistry 14 (August 8, 2018): 2082–89. http://dx.doi.org/10.3762/bjoc.14.182.

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Phosphinooxazoline (PHOX) ligands are an important class of ligands in asymmetric catalysis. We synthesized ten novel D-fructose-derived spiro-fused PHOX ligands with different steric and electronic demand. The application of two of them was tested in asymmetric allylic alkylation. The ligands are prepared in two steps from readily available 1,2-O-isopropylidene protected β-D-fructopyranoses by the BF3·OEt2-promoted Ritter reaction with 2-bromobenzonitrile to construct the oxazoline moiety followed by Ullmann coupling of the resulting aryl bromides with diphenylphosphine. Both steps proceeded
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36

Jones, Geraint, and Christopher J. Richards. "(S)-Serine derived N–O and N–P oxazoline ligands for asymmetric catalysis." Tetrahedron: Asymmetry 15, no. 4 (2004): 653–64. http://dx.doi.org/10.1016/j.tetasy.2003.11.030.

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37

Capitò, Elena, Luca Bernardi, Mauro Comes-Franchini, et al. "Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis." Tetrahedron: Asymmetry 16, no. 19 (2005): 3232–40. http://dx.doi.org/10.1016/j.tetasy.2005.08.043.

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38

Guiry, Patrick, and Steven O’Reilly. "Recent Applications of C 1-Symmetric Bis(oxazoline)-Containing Ligands in Asymmetric Catalysis." Synthesis 46, no. 06 (2014): 722–39. http://dx.doi.org/10.1055/s-0033-1340829.

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39

Pàmies, Oscar, Carmen Claver, and Montserrat Diéguez. "Phosphite–oxazoline ligands for Rh-catalyzed asymmetric hydrosilylation of ketones." Journal of Molecular Catalysis A: Chemical 249, no. 1-2 (2006): 207–10. http://dx.doi.org/10.1016/j.molcata.2006.01.019.

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40

Dawson, Graham J., Christopher G. Frost, Jonathan M. J. Williams, and Steven J. Coote. "Asymmetric palladium catalysed allylic substitution using phosphorus containing oxazoline ligands." Tetrahedron Letters 34, no. 19 (1993): 3149–50. http://dx.doi.org/10.1016/s0040-4039(00)93403-8.

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41

Richards, Christopher, and Ross Arthurs. "Synthesis of Diastereomeric Bis(oxazoline) Ligands Derived from (S,S)-1,1′-Bis(4-isopropyloxazolin-2-yl)ferrocene." Synlett 29, no. 05 (2018): 585–88. http://dx.doi.org/10.1055/s-0036-1589163.

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Starting from (S,S)-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene, all possible 2-trimethylsilyl- and 2,2′-di(trimethylsilyl)-substituted diastereoisomers, potential bisoxazoline ligands for use in asymmetric catalysis, were synthesised by selective lithiation followed by addition of trimethylsilyl chloride. Access to the (S,S,R p,R p)-diastereoisomer was achieved following diastereoselective introduction of two deuterium-blocking groups and utilisation of the high k H/k D value for lithiation, methodology that was also applied to the synthesis of a related 2,2′-di(diphenylmethanol)bisoxazoline
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42

Desimoni, Giovanni, Giuseppe Faita, and Karl Anker Joergensen. "ChemInform Abstract: Update 1 Of: C2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis." ChemInform 44, no. 52 (2013): no. http://dx.doi.org/10.1002/chin.201352250.

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43

Chakka, Sai Kumar, Byron K. Peters, Pher G. Andersson, Glenn E. M. Maguire, Hendrik G. Kruger, and Thavendran Govender. "Iridium-catalyzed asymmetric hydrogenation of olefins using TIQ phosphine–oxazoline ligands." Tetrahedron: Asymmetry 21, no. 18 (2010): 2295–301. http://dx.doi.org/10.1016/j.tetasy.2010.07.032.

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44

Sun, Siyuan, Nicolas A. Diaz, and Pavel Nagorny. "Synthesis and Evaluation of C2-Symmetric SPIROL-Based bis-Oxazoline Ligands." Symmetry 13, no. 9 (2021): 1667. http://dx.doi.org/10.3390/sym13091667.

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This communication describes the synthesis of new bis-oxazoline chiral ligands (SPIROX) derived from the C2-symmetric spirocyclic scaffold (SPIROL). The readily available (R,R,R)-SPIROL (2) previously developed by our group was subjected to a three-step sequence that provided key diacid intermediate (R,R,R)-7 in 75% yield. This intermediate was subsequently coupled with (R)- and (S)-phenylglycinols to provide diastereomeric products, the cyclization of which led to two diastereomeric SPIROX ligands (R,R,R,R,R)-3a and (R,R,R,S,S)-3b in 85% and 79% yield, respectively. The complexation of (R,R,R
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45

Newman, Louise M., Jonathan MJ Williams, Raymond McCague, and Gerard A. Potter. "Rhodium catalysed asymmetric hydrosilylation of ketones using phosphorus-containing oxazoline ligands." Tetrahedron: Asymmetry 7, no. 6 (1996): 1597–98. http://dx.doi.org/10.1016/0957-4166(96)00191-7.

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46

Wolf, Christian, and Hanhui Xu. "ChemInform Abstract: Asymmetric Catalysis with Chiral Oxazolidine Ligands." ChemInform 42, no. 31 (2011): no. http://dx.doi.org/10.1002/chin.201131229.

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47

Caputo, Christine A., Florentino d. S. Carneiro, Michael C. Jennings, and Nathan D. Jones. "Modular syntheses of oxazolinylamine ligands and characterization of group 10 metal complexes." Canadian Journal of Chemistry 85, no. 2 (2007): 85–95. http://dx.doi.org/10.1139/v06-188.

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The syntheses of aminoalkyloxazoline and pyrrolidinyloxazoline ligands, each of which bear a pair of chiral centres, by both known and new routes are reported. Variable temperature NMR studies show that the known stepwise syntheses of the pyrrolidinyl compounds are not complicated by epimerization; however, coordination of one of the aminoalkyl derivatives to Pt(II) under conditions of prolonged heating to 80 °C does give mixtures of diastereomeric N,N ′-chelated complexes that result from inversion of the chiral centre associated with the aminoalkyl fragment. A new synthesis of pyrrolidinylox
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48

Werner, Heiko, Clara I Herrerías, Michael Glos, et al. "Synthesis of Polymer Bound Azabis(oxazoline) Ligands and their Application in Asymmetric Cyclopropanations." Advanced Synthesis & Catalysis 348, no. 1-2 (2006): 125–32. http://dx.doi.org/10.1002/adsc.200505197.

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49

Liu, Duan, Qian Dai, and Xumu Zhang. "A new class of readily available and conformationally rigid phosphino-oxazoline ligands for asymmetric catalysis." Tetrahedron 61, no. 26 (2005): 6460–71. http://dx.doi.org/10.1016/j.tet.2005.03.111.

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50

O'Reilly, Steven, and Patrick J. Guiry. "ChemInform Abstract: Recent Applications of C 1-Symmetric Bis(oxazoline)-Containing Ligands in Asymmetric Catalysis." ChemInform 45, no. 23 (2014): no. http://dx.doi.org/10.1002/chin.201423251.

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