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Journal articles on the topic 'Atropisomerismo'

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Published: 11 March 2023

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1

Clayden, Jonathan. "Atropisomerism." Tetrahedron 60, no. 20 (May 2004): 4335. http://dx.doi.org/10.1016/j.tet.2004.03.002.

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2

Czarnocki, Zbigniew, and Piotr Pomarański. "Arylpyridines: A Review from Selective Synthesis to Atropisomerism." Synthesis 51, no. 03 (December 14, 2018): 587–611. http://dx.doi.org/10.1055/s-0037-1611365.

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Multiply arylated heterocycles are interesting structures with highly useful functions and fascinating optoelectronic and biological properties. Pyridines are an important class of compounds, playing a role in various fields of chemistry. When the pyridine ring is connected to other aromatic systems, novel stereochemical outcomes may arise. This work summarizes different methodologies applied for the synthesis of substituted arylpyridine derivatives and summarizes stereochemical phenomena resulting from atropisomerism present in certain arylated pyridines.1 Introduction2 Arylpyridines Containing meta- and para-Substituted Phenyl Groups2.1 Arylpyridine Derivatives as Amphetamine Analogues Markers2.2 Site-Selective Synthesis of Arylpyridines3 Atropisomerism in Arylpyridines Containing ortho-Substituted Phenyl Groups3.1 Synthesis of Arylpyridines Containing ortho-Substituted Phenyl Groups3.2 Other Methods for the Preparation of Arylated Pyridines4 Fully Substituted Pyridine Derivatives4.1 Site-Selective Synthesis of Fully Arylated Pyridines4.3 Atropisomerism in Densely Substituted Arylpyridines Containing ortho-Substituted Phenyl Groups5 Enantioselective Synthesis of Arylpyridine Derivatives6 Conclusion
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3

Siegel, Jay. "Prologue: Atropisomerism." Synlett 29, no. 16 (September 21, 2018): 2122–25. http://dx.doi.org/10.1055/s-0037-1610908.

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Jay S. Siegel received his Ph.D. from Princeton (1985), was a Swiss Universities Fellow at ETH Zurich (1983-4), and NSF–CNRS postdoctoral fellow at the University of Louis Pasteur in Strasbourg (1985-6). He began as Assistant Professor of Chemistry (1986) at UCSD, was promoted to Associate Professor (1992) and Full Professor (1996). In 2003, he was appointed as Professor and co-director of the Organic chemistry institute of the University of Zurich (UZH) and Director of its laboratory for process chemistry research (LPF). He served as Dean of Studies and Head of the Research Council for the Faculty of Sciences at UZH. He moved to Tianjin University in 2013 as dean, and joined the Schools of Pharmaceutical and Life Sciences into a new Health Science Platform. His research is in the area of Stereochemistry and Physical Organic Chemistry.
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4

Fordyce, Euan A. F., S. Fraser Hunt, Damien Crepin, Stuart T. Onions, Guillaume F. Parra, Chris J. Sleigh, John King-Underwood, Harry Finch, and John Murray. "Conformationally restricted benzothienoazepine respiratory syncytial virus inhibitors: their synthesis, structural analysis and biological activities." MedChemComm 9, no. 3 (2018): 583–89. http://dx.doi.org/10.1039/c8md00033f.

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5

Birepinte, Mélodie, Frédéric Robert, Sandra Pinet, Laurent Chabaud, and Mathieu Pucheault. "Non-biaryl atropisomerism at the C–B bond in sterically hindered aminoarylboranes." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3007–11. http://dx.doi.org/10.1039/d0ob00421a.

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6

Bischetti, Martina, Giuseppe Pomarico, Sara Nardis, Federica Mandoj, Daniel O. Cicero, and Roberto Paolesse. "5,10,15-Triarylcorrole atropisomerism." Journal of Porphyrins and Phthalocyanines 24, no. 01n03 (January 2020): 153–60. http://dx.doi.org/10.1142/s1088424619500706.

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A series of 5,10,15-triarylcorroles has been prepared, with the meso-aryl rings functionalized with different substituents to investigate their influence on the aryl ring rotation with respect to the corrole plane. The study has been carried out by different NMR techniques, allowing the complete assignment of the 1H NMR spectra and giving insights on the kinetic and thermodynamic factors driving the atropisomerism in triarylcorrole derivatives.
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7

Siegel, Jay. "Cluster Preface: Atropisomerism." Synlett 29, no. 16 (September 21, 2018): 2120–21. http://dx.doi.org/10.1055/s-0037-1610998.

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Jay S. Siegel received his Ph.D. from Princeton (1985), was a Swiss Universities Fellow at ETH Zurich (1983-4), and NSF–CNRS postdoctoral fellow at the University of Louis Pasteur in Strasbourg (1985-6). He began as Assistant Professor of Chemistry (1986) at UCSD, was promoted to Associate Professor (1992) and Full Professor (1996). In 2003, he was appointed as Professor and co-director of the Organic chemistry institute of the University of Zurich (UZH) and Director of its laboratory for process chemistry research (LPF). He served as Dean of Studies and Head of the Research Council for the Faculty of Sciences at UZH. He moved to Tianjin University in 2013 as dean and joined the Schools of Pharmaceutical and Life Sciences into a new Health Science Platform. His research is in the area of Stereochemistry and Physical Organic Chemistry.
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8

Boiadjiev, Stefan E., and David A. Lightner. "Atropisomerism in monopyrroles." Tetrahedron: Asymmetry 13, no. 16 (August 2002): 1721–32. http://dx.doi.org/10.1016/s0957-4166(02)00481-0.

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9

Ciogli, A., S. Vivek Kumar, M. Mancinelli, A. Mazzanti, S. Perumal, C. Severi, and C. Villani. "Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study." Organic & Biomolecular Chemistry 14, no. 47 (2016): 11137–47. http://dx.doi.org/10.1039/c6ob02145j.

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10

Köster, Roland, Günther Seidel, Susanna Kerschl, and Bernd Wrackmeyer. "Atropisomerism in Boron-Nitrogen Heterocycles/Atropisomerism in Boron-Nitrogen Heterocycles." Zeitschrift für Naturforschung B 42, no. 2 (February 1, 1987): 191–94. http://dx.doi.org/10.1515/znb-1987-0212.

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Abstract Atropisomerism owing to hindered rotation about the N-aryl bond is observed in 4,5-diethyl-2,2,3-trimethyl-1-(o-trifluormethyl)phenyl-2,5-dihydro-1H-1,2,5-azasila-(2) and -azastanna-boroles (5). The compounds 2 and 5 are characterized by elemental analysis, mass spectra and 1H, 11B, 13 C, 29Si and119Sn NMR. The ortho-trifluoromethyl group serves as an additional NMR spectroscopic probe because of “through space” 19F-1H and 19F-13C spin spin coupling. Compound 5 is the first derivative of a 2,5-dihydro-1H-1,2,5-azastannaborol.
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11

Meininger, Daniel J., Nicanor Muzquiz, Hadi D. Arman, and Zachary J. Tonzetich. "Synthesis, characterization, and atropisomerism of iron complexes containing the tetrakis(2-chloro-6-fluorophenyl)porphyrinate ligand." Dalton Transactions 44, no. 20 (2015): 9486–95. http://dx.doi.org/10.1039/c5dt01122a.

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12

Boiadjiev, Stefan E., and David A. Lightner. "Atropisomerism in linear tetrapyrroles." Tetrahedron 58, no. 37 (September 2002): 7411–21. http://dx.doi.org/10.1016/s0040-4020(02)00827-x.

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13

Baker, Robert W., Zinka Brkic, Melvyn V. Sargent, Brian W. Skelton, and Allan H. White. "Atropisomerism of 2,2'-Binaphthalenes." Australian Journal of Chemistry 53, no. 12 (2000): 925. http://dx.doi.org/10.1071/ch00122.

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The synthesis of diastereo-enriched substituted (4S)-4-isopropyl-2-(2,2′-binaphthalen-1-yl)-4,5-dihydrooxazoles from substituted 2-naphthalenylmagnesium bromides and (4S)-4-isopropyl-2-(2-methoxynaphthalen-1-yl)-4,5-dihydrooxazole (4) and (4S)-4-isopropyl-2-(2,3-dimethoxynaphthalen-1-yl)-4,5-dihydrooxazole (5) is described. The product oxazolines were converted into a number of derivatives and the free energy barriers to internal rotation of several of these derivatives were determined. The determination of the X-ray crystal structures and the c.d. spectra of (S,1S)-N-[2-hydroxy-1-(isopropyl)ethyl]-3-methoxy-1′,N-dimethyl-2,2′-binaphthalene-1-carboxamide (22) and (R,4S)-4-isopropyl-3-methyl-2-(1′,2′,4′-trimethyl-2,2′-binaphthalen-1-yl)-4,5-dihydrooxazolium iodide (38) allowed the assignment of the absolute configurations of all the synthetic 2,2′-binaphthalenes by comparison of their c.d. spectra with those of compounds (22) and (38).
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14

Tietze, Lutz F., Heiko J. Schuster, J. Marian von Hof, Sonja M. Hampel, Juan F. Colunga, and Michael John. "Atropisomerism of Aromatic Carbamates." Chemistry – A European Journal 16, no. 42 (September 30, 2010): 12678–82. http://dx.doi.org/10.1002/chem.201001047.

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15

Doulain, Pierre-Emmanuel, Christine Goze, Ewen Bodio, Philippe Richard, and Richard A. Decréau. "BODIPY atropisomer interconversion, face discrimination, and superstructure appending." Chemical Communications 52, no. 24 (2016): 4474–77. http://dx.doi.org/10.1039/c5cc10526a.

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Atropisomerism and atropisomer interconversion in the BODIPY series are presented. It was used to synthesize a picket-fence-like BODIPY and to examine the BODIPY face discrimination. Pickets are aimed at preventing π-stacking of the BODIPY platform.
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16

Urban, S., and RJ Capon. "Lamellarin-S: a New Aromatic Metabolite From an Australian Tunicate, Didemnum sp." Australian Journal of Chemistry 49, no. 6 (1996): 711. http://dx.doi.org/10.1071/ch9960711.

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An Australian tunicate Didemnum sp. has yielded a new alkaloid lamellarin-S (1) along with the known compound lamellarin-K (12). Of this structure class, lamellarin-S (1) is the first example that demonstrates atropisomerism , and its structure was secured by spectroscopic analysis.
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17

Ryan, Sarah J., Craig L. Francis, and G. Paul Savage. "N-Aryl Atropisomerism Induces Facial Selectivity in Benzonitrile Oxide Cycloadditions with Exocyclic Methylene Benzosultams." Australian Journal of Chemistry 66, no. 8 (2013): 874. http://dx.doi.org/10.1071/ch13270.

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N-aryl methylene benzo-fused sultams (2,3-dihydrobenzo[d]isothiazole 1,1-dioxides) underwent [3+2] cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.
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18

Allaoud, S., and B. Frange. "Atropisomerism in aryl-substituted borazines." Inorganic Chemistry 24, no. 16 (July 1985): 2520–23. http://dx.doi.org/10.1021/ic00210a011.

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19

Takahashi, Hideyo, Shintaro Wakamatsu, Hidetsugu Tabata, Tetsuta Oshitari, Ayako Harada, Keizo Inoue, and Hideaki Natsugari. "Atropisomerism Observed in Indometacin Derivatives." Organic Letters 13, no. 4 (February 18, 2011): 760–63. http://dx.doi.org/10.1021/ol103008d.

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20

Na, Lu-Xin, Xu-Lin Sun, Meng Wang, Kun-Feng Li, Lei Xing, Zhuo Chen, Zhu Guan, and Zhen-Jun Yang. "Atropisomerism of diastereomer diribonucleoside phosphotriester." Chinese Chemical Letters 24, no. 1 (January 2013): 13–16. http://dx.doi.org/10.1016/j.cclet.2013.01.018.

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21

Summers, Thomas J., Hrishikesh Tupkar, Tyler M. Ozvat, Zoë Tregillus, Kenneth A. Miller, and Nathan J. DeYonker. "Computational Insight into the Rope-Skipping Isomerization of Diarylether Cyclophanes." Symmetry 13, no. 11 (November 9, 2021): 2127. http://dx.doi.org/10.3390/sym13112127.

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The restricted rotation of chemical bonds may lead to the formation of stable, conformationally chiral molecules. While the asymmetry in chiral molecules is generally observed in the presence of one or more stereocenters, asymmetry exhibited by conformational chirality in compounds lacking stereocenters, called atropisomerism, depends on structural and temperature factors that are still not fully understood. This atropisomerism is observed in natural diarylether heptanoids where the length of the intramolecular tether constrains the compounds to isolable enantiomers at room temperature. In this work, we examine the impact tether length has on the activation free energies to isomerization of a diarylether cyclophane substructure with a tether ranging from 6 to 14 carbons. Racemization activation energies are observed to decay from 48 kcal/mol for a 7-carbon tether to 9.2 kcal/mol for a 14-carbon tether. Synthetic efforts to experimentally test these constraints are also presented. This work will likely guide the design and synthesis of novel asymmetric cyclophanes that will be of interest in the catalysis community given the importance of atropisomeric ligands in the field of asymmetric catalysis.
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22

Wang, Haimang, Jianfeng Li, and W. Robert Scheidt. "Picket fence porphyrin challenges. Unexpected atropisomerism." Journal of Porphyrins and Phthalocyanines 22, no. 11 (October 18, 2018): 981–88. http://dx.doi.org/10.1142/s1088424618500943.

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The synthesis and structural analysis of two new bis imidazole-ligated iron(II) porphyrinates are reported. The reacting porphyrin used in the studies was the four-coordinate [Formula: see text] atropisomer of [Fe(TpivPP)] (picket fence porphyrin); the axial ligands are 2-methylimidazole and 1,2-dimethylimidazole. Crystal structure analysis revealed that the [Fe(TpivPP)(2-MeHIm)[Formula: see text]] complex had a strongly ruffled porphyrin core that accommodated the hindered ligands on both the picket side and the open face of the porphyrin. Reaction with 1,2-dimethylimidazole with the four-coordinate [Fe(TpivPP)] starting material led to an isomerized form of the picket fence porphyrin. The structure analysis showed that the product obtained was the [Formula: see text] atropisomer. Strong ruffling caused by the bulky 1,2-dimethylimidazole ligand must allow the requisite rotation about the methine carbon to phenyl carbon single bond and yields what is probably the most stable form of the complex. The relative orientation of the two axial ligands in both complexes are approximately perpendicular to each other. Other structural parameters are in general accord with six-coordinate iron(II) porphyrinates.
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23

Allaoud, Smail, Touriya Zair, Abdallah Karim, and Bernard Frange. "Atropisomerism in o-aryl-substituted borazines." Inorganic Chemistry 29, no. 7 (April 1990): 1447–49. http://dx.doi.org/10.1021/ic00332a035.

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24

Crossley, Maxwell J., Leslie D. Field, Adrienne J. Forster, Margaret M. Harding, and Sever Sternhell. "Steric effects on atropisomerism in tetraarylporphyrins." Journal of the American Chemical Society 109, no. 2 (January 1987): 341–48. http://dx.doi.org/10.1021/ja00236a008.

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25

Paul, Bishwajit, Glenn L. Butterfoss, Mikki G. Boswell, Mia L. Huang, Richard Bonneau, Christian Wolf, and Kent Kirshenbaum. "N-Naphthyl Peptoid Foldamers Exhibiting Atropisomerism." Organic Letters 14, no. 3 (January 24, 2012): 926–29. http://dx.doi.org/10.1021/ol203452f.

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26

Zhang, Kan, Yuqi Liu, Zhikun Shang, Corey Evans, and Shengfu Yang. "Effects of End-Caps on the Atropisomerization, Polymerization, and the Thermal Properties of ortho-Imide Functional Benzoxazines." Polymers 11, no. 3 (March 1, 2019): 399. http://dx.doi.org/10.3390/polym11030399.

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A new type of atropisomerism has recently been discovered in 1,3-benzoxazines, where the intramolecular repulsion between negatively charged oxygen atoms on the imide and the oxazine ring hinders the rotation about the C–N bond. The imide group offers a high degree of flexibility for functionalization, allowing a variety of functional groups to be attached, and producing different types of end-caps. In this work, the effects of end-caps on the atropisomerism, thermally activated polymerization of ortho-imide functional benzoxazines, and the associated properties of polybenzoxazines have been systematically investigated. Several end-caps, with different electronic characteristics and rigidities, were designed. 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and density functional theory (DFT) calculations were employed to obtain structural information, and differential scanning calorimetry (DSC) and in situ Fourier transform infrared (FT-IR) spectroscopy were also performed to study the thermally activated polymerization process of benzoxazine monomers. We demonstrated that the atropisomerization can be switched on/off by the manipulation of the steric structure of the end-caps, and polymerization behaviors can be well-controlled by the electronic properties of the end-caps. Moreover, a trade-off effect were found between the thermal properties and the rigidity of the end-caps in polybenzoxazines.
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27

Möhrle, H., and M. Jeandrée. "Darstellung und Atropisomerie von 1-[2-(2,2-Dimethylpiperidino)phenyl]ethanol." Scientia Pharmaceutica 69, no. 1 (March 30, 2001): 1–10. http://dx.doi.org/10.3797/scipharm.aut-01-01.

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The title compound was prepared by Hg(II)-edta dehydrogenation of the aminoalkohol 2 via the benzoxazine 4, which reacted with methylmagnesiumiodide to 6. This compound shows in the NMR spectrum atropisomerism for the restricted rotation of the piperidine moiety about the aryl-C-N bond. The dehydrogenation of 6 stopped after a two electron withdrawal generating the benzoxazine 7, because the angular hydrogen atom occupies an equatorial position, which prevents stereoelectronic conditions for a further oxidation.
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28

Beattie, Nicola J., Craig L. Francis, Andris J. Liepa, and G. Paul Savage. "Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones." Australian Journal of Chemistry 63, no. 3 (2010): 445. http://dx.doi.org/10.1071/ch09479.

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Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.
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29

Gu, Zhenhua, and Jia Feng. "Atropisomerism in Styrene: Synthesis, Stability, and Applications." SynOpen 05, no. 01 (January 2021): 68–85. http://dx.doi.org/10.1055/s-0040-1706028.

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AbstractAtropisomeric styrenes are a class of optically active compounds, the chirality of which results from restricted rotation of the C(vinyl)–C(aryl) single bond. In comparison with biaryl atropisomers, the less rigid skeleton of styrenes usually leads them to have lower rotational barriers. Although it has been overlooked for a long time, scientists have paid attention to this class of unique molecules in recent years and have developed many methods for the preparation of optically active atropisomeric styrenes. In this article, we review the development of the concept of atropisomeric styrenes, along with their isolation, asymmetric synthesis, and synthetic applications.1 Introduction2 The Concept of Styrene Atropisomerism3 Early Research: Separation of Optically Active Styrenes4 Synthesis of Optically Active Styrenes5 Stability of the Chirality of Atropisomeric Styrenes6 Outlook
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30

Toenjes, Sean T., and Jeffrey L. Gustafson. "Atropisomerism in medicinal chemistry: challenges and opportunities." Future Medicinal Chemistry 10, no. 4 (February 2018): 409–22. http://dx.doi.org/10.4155/fmc-2017-0152.

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31

Consoli, Grazia M. L., Francesca Cunsolo, Corrada Geraci, Enrico Gavuzzo, and Placido Neri. "Atropisomerism in 1,5-Bridged Calix[8]arenes†." Organic Letters 4, no. 16 (August 2002): 2649–52. http://dx.doi.org/10.1021/ol026185r.

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32

Alcock, Nathaniel W., John M. Brown, and Jesús J. Pérez-Torrente. "Atropisomerism in asymmetric cis-diphosphine arylplatinum complexes." Tetrahedron Letters 33, no. 3 (January 1992): 389–92. http://dx.doi.org/10.1016/s0040-4039(00)74139-6.

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33

Veljković, Jelena, Ivana Antol, Nikola Basarić, Vilko Smrečki, Krešimir Molčanov, Norbert Müller, and Kata Mlinarić-Majerski. "Atropisomerism in 1-(2-adamantyl)naphthalene Derivatives." Journal of Molecular Structure 1046 (August 2013): 101–9. http://dx.doi.org/10.1016/j.molstruc.2013.04.027.

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34

Glunz, Peter W. "Recent encounters with atropisomerism in drug discovery." Bioorganic & Medicinal Chemistry Letters 28, no. 2 (January 2018): 53–60. http://dx.doi.org/10.1016/j.bmcl.2017.11.050.

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35

Clayden, Jonathan, Wesley J Moran, Paul J Edwards, and Steven R LaPlante. "The Challenge of Atropisomerism in Drug Discovery." Angewandte Chemie International Edition 48, no. 35 (August 17, 2009): 6398–401. http://dx.doi.org/10.1002/anie.200901719.

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36

Constable, Edwin C., Richard M. Hartshorn, and Catherine E. Housecroft. "1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections." Molecules 26, no. 6 (March 13, 2021): 1584. http://dx.doi.org/10.3390/molecules26061584.

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1,1′-Biisoquinolines are a class of bidentate nitrogen donor ligands in the heterocyclic diimine family. This review briefly discusses their properties and the key synthetic pathways available and then concentrates upon their coordination behaviour. The ligands are of interest as they exhibit the phenomenon of atropisomerism (hindered rotation about the C1–C1′ bond). A notation for depicting the stereochemistry in coordination compounds containing multiple stereogenic centers is developed. The consequences of the chirality within the ligand on the coordination behaviour is discussed in detail.
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37

Carroll, AR, and WC Taylor. "Constituents of Eupomatia Species. xiv. The Structures of Eupomatilone-1, -2, -3, -4, -5, -6 and -7 Isolated From Eupomatia Bennettii." Australian Journal of Chemistry 44, no. 12 (1991): 1705. http://dx.doi.org/10.1071/ch9911705.

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On the basis of spectroscopic evidence, the eupomatilones (from eupomatilone-1 to -7) isolated from Eupomatia bennettii F. Muell. were shown to be degraded lignans . Eupomatilone-1 was assigned the structure (1), cis-4-methyl-3-methylene-5-(3″,4″,5″,6′-tetramethoxy-4′,5′-methylenedioxybiphenyl-2′-yl)dihydrofuran-2(3H)-one. The other six eupomatilones differ from eupomatilone-1 either in the degree of oxygenation of the biphenyl system or in the substitution of the furanone ring. Atropisomerism was observed with the compounds.
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38

Ryan, Sarah J., Craig L. Francis, and G. Paul Savage. "Benzonitrile Oxide Cycloadditions with Exocyclic Methylene Benzothiazepine Dioxides." Australian Journal of Chemistry 67, no. 3 (2014): 381. http://dx.doi.org/10.1071/ch13444.

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N-substituted 5-methylene-2,3,4,5-tetrahydrobenzo[f][1,2]thiazepine 1,1-dioxides underwent 1,3-dipolar cycloaddition with benzonitrile oxide, generated in situ, to give isoxazoline spiro adducts. The cycloadditions were completely regioselective to give the hitherto unreported 3,4-dihydro-2H,4′H-spiro[benzo[f][1,2]thiazepine-5,5′-isoxazole] 1,1-dioxide cycloadduct. Where the N-substituent on the sulfonamide cycloaddition precursor was a 2-substituted arene, the resulting atropisomerism along the N-aryl bond led to facial selectivity in the cycloaddition reaction, with greater than 90 % diastereoselectivity.
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39

Alkorta, Ibon, José Elguero, Artur M. S. Silva, and Augusto C. Tomé. "A theoretical study of the conformation of meso-tetraphenylporphyrin (TPPH2), its anions, cations and metal complexes (Mg2+, Ca2+ and Zn2+)." Journal of Porphyrins and Phthalocyanines 14, no. 07 (July 2010): 630–38. http://dx.doi.org/10.1142/s1088424610002409.

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A theoretical study has been carried out on TPPH2 (both tautomers), its deprotonated and protonated forms, as well as complexes of TPP containing Mg 2+, Ca 2+ and Zn 2+ ions. Two properties have been analyzed. The first one considers the conformation of the meso-phenyl rings and the deformation of the porphyrin macrocycle, the second one relates to the barriers of rotation of the meso-phenyl rings (atropisomerism). In the case of the Zn complex ( ZnTPP ), the coordination effects with the N3 of 1H-imidazole have been calculated.
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40

Tomé, Augusto C., Artur M. S. Silva, Ibon Alkorta, and José Elguero. "Atropisomerism and conformational aspects of meso-tetraarylporphyrins and related compounds." Journal of Porphyrins and Phthalocyanines 15, no. 01 (January 2011): 1–28. http://dx.doi.org/10.1142/s1088424611002994.

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This review provides a comprehensive description of the atropisomerism of meso-di- and tetraarylporphyrins with substituents in ortho-positions of the aryl ring, as well as in corroles and in conveniently substituted phthalocyanines. Different methods of study were examined: X-ray crystallography, NMR spectroscopy (both static and dynamic aspects), classical kinetics, HPLC and theoretical calculations. Then the four atropisomers, the tautomerism of the inner protons, the 'picket fence' concept, conformationally restricted meso-tetraarylporphyrins and the influence of the metal on the conformation were discussed based on 250 references.
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41

Lloyd-Williams, Paul, and Ernest Giralt. "Atropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics." Chemical Society Reviews 30, no. 3 (2001): 145–57. http://dx.doi.org/10.1039/b001971m.

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42

Boger, Dale L., Steven L. Castle, Susumu Miyazaki, Jason H. Wu, Richard T. Beresis, and Olivier Loiseleur. "Vancomycin CD and DE Macrocyclization and Atropisomerism Studies." Journal of Organic Chemistry 64, no. 1 (January 1999): 70–80. http://dx.doi.org/10.1021/jo980880o.

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43

Nakamura, Takashi, Nobuaki Waizumi, Koichi Tsuruta, Yoshiaki Horiguchi, and Isao Kuwajima. "Synthesis of the Taxol Derivatives: Control of Atropisomerism." Synlett 1994, no. 08 (1994): 584–86. http://dx.doi.org/10.1055/s-1994-22934.

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44

Wang, C. H., J. Reilly, N. Brand, S. Schwartz, S. Alluri, T. M. Chan, A. V. Buevich, and A. K. Ganguly. "Synthesis and atropisomerism of 2,2′-ortho disubstituted biphenyls." Tetrahedron Letters 51, no. 48 (December 2010): 6213–15. http://dx.doi.org/10.1016/j.tetlet.2010.09.010.

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45

Howarth, Ashlee J., David L. Davies, Francesco Lelj, Michael O. Wolf, and Brian O. Patrick. "Atropisomerism in a thermally switchable, cyclometallated iridium complex." Dalton Transactions 41, no. 34 (2012): 10150. http://dx.doi.org/10.1039/c2dt31120h.

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46

Seifert, Nathan A., Cristóbal Pérez, Justin L. Neill, Brooks H. Pate, Montserrat Vallejo-López, Alberto Lesarri, Emilio J. Cocinero, and Fernando Castaño. "Chiral recognition and atropisomerism in the sevoflurane dimer." Physical Chemistry Chemical Physics 17, no. 28 (2015): 18282–87. http://dx.doi.org/10.1039/c5cp01025j.

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47

Nguyen, Thanh V, David J Sinclair, Anthony C Willis, and Michael S Sherburn. "Guest Binding Drives Reversible Atropisomerism in Cavitand Hosts." Chemistry - A European Journal 15, no. 24 (June 8, 2009): 5892–95. http://dx.doi.org/10.1002/chem.200900695.

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48

O’Connor, Stephen P., Ying Wang, Ligaya M. Simpkins, Robert P. Brigance, Wei Meng, Aiying Wang, Mark S. Kirby, Carolyn A. Weigelt, and Lawrence G. Hamann. "Synthesis, SAR, and atropisomerism of imidazolopyrimidine DPP4 inhibitors." Bioorganic & Medicinal Chemistry Letters 20, no. 21 (November 2010): 6273–76. http://dx.doi.org/10.1016/j.bmcl.2010.08.090.

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49

Roszkowski, Piotr, Dariusz Błachut, Jan K. Maurin, Magdalena Woźnica, Jadwiga Frelek, Franciszek Pluciński, and Zbigniew Czarnocki. "Atropisomerism in 3,4,5-Tri-(2-methoxyphenyl)-2,6-lutidine." European Journal of Organic Chemistry 2013, no. 35 (November 12, 2013): 7867–71. http://dx.doi.org/10.1002/ejoc.201301378.

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50

Ontiveros-Rodríguez, Julio C., Eleuterio Burgueño-Tapia, Javier Porras-Ramírez, Pedro Joseph-Nathan, and L. Gerardo Zepeda. "Configurational Study of an Aporphine Alkaloid from Annona purpurea." Natural Product Communications 13, no. 7 (July 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300711.

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Purpureine (1), norpurpureine (2), and 3-hydroxyglaucine (4) were isolated from the leaves of Annona purpurea. A vibrational circular dichroism study for the absolute configuration determination of 1 provides evidence for the mutually dependent atropisomerism, local chirality of the sole stereogenic center, and the geometry of the tetrahedral nitrogen atom in aporphine alkaloids. The observed change in the optical rotation sign between 2 and its hydrochloride 3 might explain why this compound has been reported as dextrorotatory and levorotatory from the same botanical source. Furthermore, 1H and 13C NMR spectra of 1, 2 and 4 were fully assigned for the first time.
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