Stereoselectively fluorinated N-heterocycles: a brief survey

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• Renault, Y. J. G.; Diao, J.; Cordes, D. B.; Leach, K.; O'Hagan, D. Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendiline and NPS R-467. Medicinal Chemistry Research 2023, 32, 1532–1542. doi:10.1007/s00044-023-03103-0
• Renault, Y. J. G.; Diao, J.; Cordes, B. B.; Leach, K.; O'Hagan, D. Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendilines and NPS R-467. Research Square Platform LLC 2023. doi:10.21203/rs.3.rs-2937250/v1
• Sonet, D.; Cayla, M.; Méreau, R.; Morvan, E.; Lacoudre, A.; Vanthuyne, N.; Albalat, M.; Bassani, D. M.; Scalabre, A.; Pouget, E.; Bibal, B. Chiral Anthranyl Trifluoromethyl Alcohols: Structures, Oxidative Dearomatization and Chiroptical Properties. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202202695. doi:10.1002/chem.202202695
• Schaub, S.; Becker, J.; Schindler, S. A Facile and Inexpensive Way to Synthesize N‐trifluoromethyl Compounds. ChemistrySelect 2022, 7. doi:10.1002/slct.202201803
• Li, Y.-X.; Wang, J.-Z.; Shimadate, Y.; Kise, M.; Kato, A.; Jia, Y.-M.; Fleet, G. W. J.; Yu, C.-Y. Diastereoselective Synthesis, Glycosidase Inhibition, and Docking Study of C-7-Fluorinated Casuarine and Australine Derivatives. The Journal of organic chemistry 2022, 87, 7291–7307. doi:10.1021/acs.joc.2c00485
• Wannenmacher, N.; Pfeffer, C.; Frey, W.; Peters, R. Enantioenriched γ-Aminoalcohols, β-Amino Acids, β-Lactams, and Azetidines Featuring Tetrasubstituted Fluorinated Stereocenters via Palladacycle-Catalyzed Asymmetric Fluorination of Isoxazolinones. The Journal of organic chemistry 2021, 87, 670–682. doi:10.1021/acs.joc.1c02640
• Kiss, L.; Ouchakour, L.; Nonn, M.; Remete, A. M. Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles. Synlett 2021, 33, 307–328. doi:10.1055/s-0040-1719850
• Utecht-Jarzyńska, G.; Nagła, K.; Mlostoń, G.; Heimgartner, H.; Palusiak, M.; Jasiński, M. A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines. Beilstein journal of organic chemistry 2021, 17, 1509–1517. doi:10.3762/bjoc.17.108
• Ouchakour, L.; Nonn, M.; Remete, A. M.; Kiss, L. An Improved Stereocontrolled Access Route to Piperidine or Azepane β-Amino Esters and Azabicyclic β- and γ-Lactams; Synthesis of Novel Functionalized Azaheterocyles. European Journal of Organic Chemistry 2021, 2021, 3874–3885. doi:10.1002/ejoc.202100540
• Yashwantrao, G.; Saha, S. Recent advances in the synthesis and reactivity of quinoxaline. Organic Chemistry Frontiers 2021, 8, 2820–2862. doi:10.1039/d0qo01575j
• Ye, F.; Ge, Y.; Spannenberg, A.; Neumann, H.; Beller, M. The role of allyl ammonium salts in palladium-catalyzed cascade reactions towards the synthesis of spiro-fused heterocycles. Nature communications 2020, 11, 5383. doi:10.1038/s41467-020-19110-3
• Chen, S.; Ruan, Y.; Lu, J.-L.; Hunter, L.; Hu, X.-G. Diastereoselective synthesis and conformational analysis of 4,5-difluoropipecolic acids. Organic & biomolecular chemistry 2020, 18, 8192–8198. doi:10.1039/d0ob01811b
• Luzzio, F. A. Synthesis and reactivity of fluorinated heterocycles. Advances in Heterocyclic Chemistry; Elsevier, 2020; Vol. 132, pp 1–84. doi:10.1016/bs.aihch.2020.02.001
• Ghosez, L. A lifetime journey into the world of chemistry. Tetrahedron 2019, 75, 130345. doi:10.1016/j.tet.2019.05.024
• Zou, L.; Ruan, Y.; Jiang, W.; Yan, N.; Liu, D.-Y.; Yu, C.-Y.; Hu, X.-G. Switchable Regioselectivity in the Opening of Aziridine by Fluoride: DFT Calculation and Synthesis of Fluorinated Piperidines. ChemistrySelect 2019, 4, 12683–12688. doi:10.1002/slct.201903403
• Bilska-Markowska, M.; Szwajca, A.; Marciniak, B. Design, properties and applications of fluorinated and fluoroalkylated N-containing monosaccharides and their analogues. Journal of Fluorine Chemistry 2019, 227, 109364. doi:10.1016/j.jfluchem.2019.109364
• Kiss, L.; Ouchakour, L.; Abrahami, R. A.; Nonn, M. Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols. Chemical record (New York, N.Y.) 2019, 20, 120–141. doi:10.1002/tcr.201900025
• Utecht-Jarzyńska, G.; Michalak, A.; Banaś, J.; Mlostoń, G.; Jasiński, M. Trapping of trifluoroacetonitrile imines with mercaptoacetaldehyde and mercaptocarboxylic acids: An access to fluorinated 1,3,4-thiadiazine derivatives via (3+3)-annulation. Journal of Fluorine Chemistry 2019, 222-223, 8–14. doi:10.1016/j.jfluchem.2019.04.012
• Fawcett, A.; Murtaza, A.; Gregson, C. H. U.; Aggarwal, V. K. Strain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines. Journal of the American Chemical Society 2019, 141, 4573–4578. doi:10.1021/jacs.9b01513
• Hardianto, A.; Khanna, V.; Liu, F.; Ranganathan, S. Diverse dynamics features of novel protein kinase C (PKC) isozymes determine the selectivity of a fluorinated balanol analogue for PKCε. BMC bioinformatics 2019, 19, 342. doi:10.1186/s12859-018-2373-1

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