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Littérature scientifique sur le sujet « C–N atropisomers »

Auteur : Grafiati

Publié le 30 novembre 2024

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Articles de revues sur le sujet "C–N atropisomers"

Xiao, Xiao, Biao Chen, Yi-Ping Yao, Hai-Jie Zhou, Xu Wang, Neng-Zhong Wang et Fen-Er Chen. « Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis ». Molecules 27, n^o 19 (4 octobre 2022) : 6583. http://dx.doi.org/10.3390/molecules27196583.

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The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of catalytic atroposelective approaches has been reported for the efficient construction of these challenging scaffolds. However, greatly concise and highly useful methodologies for the synthesis of these atropisomeric compounds, focusing on transition-metal, chiral amine, and phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly and systematically present all such reports by means of disclosing the mechanistic analysis and application, as well as the challenges and issues associated with the establishment of these atropisomers. In this review, we summarize the development of catalytic asymmetric synthetic strategies to access non-biaryl atropisomers rotating around a C–N chiral axis, including the reaction methods, mechanism, late-stage transformations, and applications.

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Bonne, Damien, et Jean Rodriguez. « Enantioselective syntheses of atropisomers featuring a five-membered ring ». Chemical Communications 53, n^o 92 (2017) : 12385–93. http://dx.doi.org/10.1039/c7cc06863h.

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If six-membered ring biaryl or heterobiaryl atropisomers are the most common ones, the focus of this feature article will be put on the enantioselective approaches towards five-membered ring containing atropisomers displaying either a stereogenic C–N- or C–C bond.

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Wang, Donglei, Qianwen Jiang et Xiaoyu Yang. « Atroposelective synthesis of configurationally stable nonbiaryl N–C atropisomers through direct asymmetric aminations of 1,3-benzenediamines ». Chemical Communications 56, n^o 46 (2020) : 6201–4. http://dx.doi.org/10.1039/d0cc02368j.

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Faisca Phillips, Ana Maria, et Armando J. L. Pombeiro. « Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen along the Axis of Chirality ». Symmetry 15, n^o 6 (15 juin 2023) : 1261. http://dx.doi.org/10.3390/sym15061261.

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Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or by electrostatics, may interact with their surroundings in different ways, and may also exhibit different properties. They may be found as natural products, as pharmaceutical or agricultural active ingredients, as chiral ligands and organocatalysts, and in functional materials. Our ability to synthesize them stereoselectively and in a sustainable way, using achiral materials and simply with the aid of an organocatalyst and mild conditions, has become a hot topic in research. This review provides an overview of recent achievements in the synthesis of atropisomers containing C-N and N-N axes of chirality.

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Jiayong, Zhang, et Liu Xin-Yuan. « Single-Step Synthesis of Atropisomers with Vicinal C—C and C—N Diaxes via Cobalt-Catalyzed C—H Activation ». Chinese Journal of Organic Chemistry 42, n^o 11 (2022) : 3899. http://dx.doi.org/10.6023/cjoc202200062.

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Monteiro, Carlos J. P., Mariette M. Pereira, Nuno P. F. Gonçalves, Carla G. Carvalho, Ângela C. B. Neves, Artur R. Abreu, Luis G. Arnaut et Artur M. S. Silva. « Separation and atropisomer isolation of ortho-halogenated tetraarylporphyrins by HPLC : Full characterization using 1D and 2D NMR ». Journal of Porphyrins and Phthalocyanines 16, n^o 03 (mars 2012) : 316–23. http://dx.doi.org/10.1142/s1088424612500368.

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The separation and isolation of the four atropisomers of ortho-halogenated tetraarylporphyrins by semi-preparative HPLC is described. Full characterization and assignment of all 1 H and 13 C resonances of 5,10,15,20-tetrakis(2-fluoro or 2-chlorophenyl)porphyrins and 5,10,15,20-tetrakis(2-fluoro or chloro-5-N-ethylsulfamoylphenyl)porphyrins by 1D and 2D NMR techniques is reported. The outcome is an unequivocal evidence of the chlorosulfonation of meso-tetra(2-haloaryl)porphyrins on the 5′-position.

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Jia, Zhen-Sheng, Yong-Jie Wu, Qi-Jun Yao, Xue-Tao Xu, Kun Zhang et Bing-Feng Shi. « Pd(II)-Catalyzed Atroposelective C–H Allylation : Synthesis of Enantioenriched N-Aryl Peptoid Atropisomers ». Organic Letters 24, n^o 1 (29 décembre 2021) : 304–8. http://dx.doi.org/10.1021/acs.orglett.1c03967.

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Wu, Yong-Jie, Pei-Pei Xie, Gang Zhou, Qi-Jun Yao, Xin Hong et Bing-Feng Shi. « Atroposelective synthesis of N-aryl peptoid atropisomers via a palladium(ii)-catalyzed asymmetric C–H alkynylation strategy ». Chemical Science 12, n^o 27 (2021) : 9391–97. http://dx.doi.org/10.1039/d1sc01130h.

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Hasegawa, Futoshi, Kazushi Kawamura, Hiroshi Tsuchikawa et Michio Murata. « Stable C–N axial chirality in 1-aryluracil scaffold and differences in in vitro metabolic clearance between atropisomers of PDE4 inhibitor ». Bioorganic & ; Medicinal Chemistry 25, n^o 16 (août 2017) : 4506–11. http://dx.doi.org/10.1016/j.bmc.2017.06.042.

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Bain, Alex D., Hao Chen et Paul H. M. Harrison. « Studies of structure and dynamics in a nominally symmetric twisted amide by NMR and electronic structure calculations ». Canadian Journal of Chemistry 84, n^o 3 (1 mars 2006) : 421–28. http://dx.doi.org/10.1139/v06-016.

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Amides that are twisted around the C—N bond show unusual spectroscopy and reactivity when compared with planar amides. The diacyl derivatives of 3,4,7,8-tetramethyl-2,5-dithioglycoluril are intriguing examples of this class, since the crystal structures show that the two acyl groups are twisted by different amounts on either side of the molecule owing to a combination of steric and electronic effects. However, the 1H NMR spectra in solution at room temperature exhibit only one acyl resonance, so there must be fast interconversion among pairs of equivalent structures of each compound. We have prepared a number of derivatives with different acyl groups, both on the glycoluril framework as well as on its dithio analogue. The chemical exchange in solution was slowed down sufficiently by cooling to see individual sites for only two compounds: the dithiodipivaloyl and the dithiodiadamantyl derivatives. The barriers were estimated at 41 kJ mol–1 for the dipivaloyl derivative and 45 kJ mol–1 for diadamantyl derivative. The results show that rotation around the twisted amide bond is slowed by both the steric size of the acyl group and the presence of the thioureido group vs. the ureido group in the glycoluril core. In the solid-state 13C NMR spectra, there is no evidence for any dynamics, even for the diacetyl derivative at ambient temperature. Electronic structure calculations predict a geometry for the dipivaloyl derivative very close to that observed in the crystal structure. These results indicate that the crystal confines, but does not distort the molecule. A mechanism for the exchange is proposed. The relevance of these results to the mechanism of Claisen-like condensations in diacylglycolurils is also discussed.Key words: 1H and 13C NMR, exchange, dynamics, CP/MAS, solids, line shape analysis, amides, twisted amides, atropisomers, glycoluril.

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Thèses sur le sujet "C–N atropisomers"

Marchal, Lucas. « Synthèse de nouveaux candidats médicamenteux présentant une chiralité axiale C-N par le développement de nouveaux couplages C-N atroposélectifs ». Electronic Thesis or Diss., Strasbourg, 2024. http://www.theses.fr/2024STRAF029.

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Les composés à chiralité axiale C–N ont démontré un potentiel significatif dans divers domaines, en particulier dans l'industrie pharmaceutique. Cependant, il existe actuellement peu de méthodologies connues permettant d’accéder à ces composés, et elles sont généralement limitées à des structures moléculaires très spécifiques. Afin de préparer de nouveaux atropisomères C–N d'intérêt, des méthodologies synthétiques innovantes doivent être développées. À cette fin, nous avons concentré nos efforts sur l'utilisation de sels de diaryliodonium comme partenaires de couplage hautement réactifs, ce qui nous a permis de concevoir un nouveau couplage C–N atropo-énantiosélectif catalysé au cuivre pour obtenir des benzoxazolones N-arylées énantio-enrichies. Les applications potentielles bioactives de ces molécules ont été étudiées et des études mécanistiques ont été menées pour concevoir un cycle catalytique pour ce couplage. De telles investigations approfondies ont été possibles grâce à une collaboration interdisciplinaire fructueuse. Le développement de nouvelles méthodologies a été étendu au premier couplage C–N atropo-énantiosélectif photoinduit
C–N axially chiral compounds have demonstrated significant potential across various fields, especially in the pharmaceutical industry. However, there are currently only few known methodologies to access these compounds, which are generally restricted to very specific molecular scaffolds. In order to prepare new C–N atropisomers of interest, innovative synthetic methodologies must be develop. To this purpose, we focused our efforts of the use of diaryliodonium salts as highly reactive coupling partners which allowed us to design a new copper-catalyzed atropo-enantioselective C–N coupling to afford enantio-enriched N-aryl benzoxazolones. The potential bioactive applications of such molecules has been studied and mechanistic studies were carried out to design a catalytic cycle for coupling. Such in-depth investigations were possible thanks to a fruitful interdisciplinary collaboration. The development of new methodologies was further extended through the first photoinduced atropo-enantioselective C–N coupling

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