Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates

Loránd Kiss, Melinda Nonn, Reijo Sillanpää, Santos Fustero and Ferenc Fülöp
Beilstein J. Org. Chem. 2013, 9, 1164–1169. https://doi.org/10.3762/bjoc.9.130

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Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates
Loránd Kiss, Melinda Nonn, Reijo Sillanpää, Santos Fustero and Ferenc Fülöp
Beilstein J. Org. Chem. 2013, 9, 1164–1169. https://doi.org/10.3762/bjoc.9.130

How to Cite

Kiss, L.; Nonn, M.; Sillanpää, R.; Fustero, S.; Fülöp, F. Beilstein J. Org. Chem. 2013, 9, 1164–1169. doi:10.3762/bjoc.9.130

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Scholarly Works

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  • Miles, S. A.; Nillama, J. A.; Hunter, L. Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains. Molecules (Basel, Switzerland) 2023, 28, 6192. doi:10.3390/molecules28176192
  • Kiss, L.; NOVÁK, T.; ARADI, K.; NONN, M.; Gömöry, Á.; Hornyánszky, G. Studies on Fluorofunctionalization of Some Functionalized Alkene Scaffolds. Elsevier BV 2023. doi:10.2139/ssrn.4661748
  • Kiss, L.; NOVÁK, T.; ARADI, K.; NONN, M.; Gömöry, Á.; Hornyánszky, G. Studies on Fluorofunctionalization of Some Functionalized Alkene Scaffolds. Elsevier BV 2023. doi:10.2139/ssrn.4585335
  • Brittain, W. D. G.; Lloyd, C. M.; Cobb, S. L. Synthesis of complex unnatural fluorine-containing amino acids. Journal of fluorine chemistry 2020, 239, 109630. doi:10.1016/j.jfluchem.2020.109630
  • Remete, A. M.; Novák, T. T.; Nonn, M.; Haukka, M.; Fülöp, F.; Kiss, L. Synthesis of novel fluorinated building blocks via halofluorination and related reactions. Beilstein journal of organic chemistry 2020, 16, 2562–2575. doi:10.3762/bjoc.16.208
  • Remete, A. M.; Nonn, M.; Fustero, S.; Haukka, M.; Fülöp, F.; Kiss, L. Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence. Beilstein journal of organic chemistry 2017, 13, 2364–2371. doi:10.3762/bjoc.13.233
  • Kiss, L.; Fülöp, F. Selective Synthesis of Fluorine-Containing Cyclic β-Amino Acid Scaffolds. Chemical record (New York, N.Y.) 2017, 18, 266–281. doi:10.1002/tcr.201700038
  • Kiss, L.; Mándity, I. M.; Fülöp, F. Highly functionalized cyclic β-amino acid moieties as promising scaffolds in peptide research and drug design. Amino acids 2017, 49, 1441–1455. doi:10.1007/s00726-017-2439-9
  • Kiss, L.; Nonn, M.; Sillanpää, R.; Haukka, M.; Fustero, S.; Fülöp, F. Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids. Chemistry, an Asian journal 2016, 11, 3376–3381. doi:10.1002/asia.201601046
  • Kiss, L.; Remete, A. M.; Nonn, M.; Fustero, S.; Sillanpää, R.; Fülöp, F. Substrate-dependent fluorinations of highly functionalized cycloalkanes. Tetrahedron 2016, 72, 781–787. doi:10.1016/j.tet.2015.12.017
  • Kiss, L.; Forró, E.; Orsy, G.; Abrahami, R. A.; Fülöp, F. Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives. Molecules (Basel, Switzerland) 2015, 20, 21094–21102. doi:10.3390/molecules201219749
  • Aparici, I.; Guerola, M.; Dialer, C.; Simón-Fuentes, A.; Sánchez-Roselló, M.; del Pozo, C.; Fustero, S. Diastereodivergent Synthesis of Fluorinated Cyclic β3-Amino Acid Derivatives. Organic letters 2015, 17, 5412–5415. doi:10.1021/acs.orglett.5b02759
  • Meng, Q.; Liu, N.; Huang, B.; Zhan, P.; Liu, X. Novel fluorine-containing DAPY derivatives as potent HIV-1 NNRTIs: a patent evaluation of WO2014072419. Expert opinion on therapeutic patents 2015, 25, 1477–1486. doi:10.1517/13543776.2016.1088832
  • Nonn, M.; Kiss, L.; Forró, E.; Sillanpää, R.; Fülöp, F. Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: orthogonally protected di- and triaminocyclopentanecarboxylates. Tetrahedron 2014, 70, 8511–8519. doi:10.1016/j.tet.2014.09.071
  • Kiss, L.; Nonn, M.; Forró, E.; Sillanpää, R.; Fustero, S.; Fülöp, F. A Selective Synthesis of Fluorinated Cispentacin Derivatives. European Journal of Organic Chemistry 2014, 2014, 4070–4076. doi:10.1002/ejoc.201402121

Patents

  • BALAN GAYATRI; BLOMGREN PETER A; CHEN CHEN; CODELLI JULIAN A; DU ZHIMIN; KIM MUSONG; SADDIER AXE DOROTHÉE; SCHWARZWALDER GREGG M; THOMAS-TRAN RHIANNON; TUDESCO MICHAEL T; VENKATARAMANI CHANDRASEKAR; WATKINS WILLIAM J; WEIST BRIAN M; YEUNG SUET C; YU HELEN. IKAROS ZINC FINGER FAMILY DEGRADERS AND USES THEREOF. WO 2023178181 A1, Sept 21, 2023.
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