Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

Melinda Nonn, Loránd Kiss, Reijo Sillanpää and Ferenc Fülöp
Beilstein J. Org. Chem. 2012, 8, 100–106. https://doi.org/10.3762/bjoc.8.10

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Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines
Melinda Nonn, Loránd Kiss, Reijo Sillanpää and Ferenc Fülöp
Beilstein J. Org. Chem. 2012, 8, 100–106. https://doi.org/10.3762/bjoc.8.10

How to Cite

Nonn, M.; Kiss, L.; Sillanpää, R.; Fülöp, F. Beilstein J. Org. Chem. 2012, 8, 100–106. doi:10.3762/bjoc.8.10

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  • Kiss, L.; Benke, Z.; Nonn, M.; Remete, A. M.; Fustero, S. Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction. Synlett 2021, 32, 1911–1933. doi:10.1055/s-0040-1706041
  • Kiss, L.; Benke, Z.; Remete, A. M.; Fülöp, F. Diversity-oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring-opening/Cross-metathesis Protocols; Transformation of a "Flatland" into Three-dimensional Scaffolds With Stereo- and Regiocontrol. Chemical record (New York, N.Y.) 2020, 20, 1129–1141. doi:10.1002/tcr.202000070
  • Otero, J. M.; Estévez, A. M.; Estévez, J. C.; Fleet, G. W. J.; Estévez, R. J. Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters. Tetrahedron 2020, 76, 130837. doi:10.1016/j.tet.2019.130837
  • Benke, Z.; Nonn, M.; Fülöp, F.; Kiss, L. An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3‐Dipolar Cycloadditions. ChemistrySelect 2019, 4, 2886–2891. doi:10.1002/slct.201900688
  • Remete, A. M.; Nonn, M.; Fustero, S.; Fülöp, F.; Kiss, L. Synthesis of fluorinated amino acid derivatives through late-stage deoxyfluorinations. Tetrahedron 2018, 74, 6367–6418. doi:10.1016/j.tet.2018.09.021
  • 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
  • Ospina, J.; Gutiérrez-Abad, R.; Lope-Piedrafita, S.; Illa, O.; Branchadell, V.; Ortuño, R. M. Stereoselective synthesis of highly branched chiral cyclobutane-cored triamines and their conjugation to Gd-DOTA. Tetrahedron 2015, 71, 8085–8095. doi:10.1016/j.tet.2015.08.044
  • Pilsl, L. K. A. Ph.D. Thesis, May 8, 2015.
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  • Panda, A.; Das, S.; Pal, S. Highly regio- and diastereoselective, acidic clay supported intramolecular nitrile oxide-alkene cycloaddition on D-ribose derived nitriles: an efficient synthetic route to isoxazoline fused five and six membered carbocycles. Carbohydrate research 2014, 398, 13–18. doi:10.1016/j.carres.2014.06.007
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  • Gonçalves, R. S. B.; Dos Santos, M.; Bernadat, G.; Bonnet-Delpon, D.; Crousse, B. A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime. Beilstein journal of organic chemistry 2013, 9, 2387–2394. doi:10.3762/bjoc.9.275
  • Würdemann, M.; Christoffers, J. Nitrile Oxide versus Nitrone – Switching Regioselectivity of Intramolecular 1,3‐Dipolar Cycloadditions towards the Preparation of Aminopiperidinecarboxylates. European Journal of Organic Chemistry 2013, 2013, 7421–7431. doi:10.1002/ejoc.201301039
  • Kiss, L.; Nonn, M.; Sillanpää, R.; Fustero, S.; Fülöp, F. Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates. Beilstein journal of organic chemistry 2013, 9, 1164–1169. doi:10.3762/bjoc.9.130
  • Gecse, Z.; Ilisz, I.; Nonn, M.; Grecsó, N.; Fülöp, F.; Agneeswari, R.; Hyun, M. H.; Péter, A. High-performance liquid chromatographic enantioseparation of isoxazoline-fused 2-aminocyclopentanecarboxylic acids on a chiral ligand-exchange stationary phase. Journal of separation science 2013, 36, 1335–1342. doi:10.1002/jssc.201201061
  • Alcaide, B.; Almendros, P. Four-Membered Ring Systems. Progress in Heterocyclic Chemistry; Elsevier, 2013; pp 71–96. doi:10.1016/b978-0-08-099406-2.00003-0
  • Cherepanova, M.; Kiss, L.; Sillanpää, R.; Fülöp, F. Synthesis of novel functionalized cispentacins through C–C oxidative cleavage of diendo-norbornene β-amino acid. RSC Advances 2013, 3, 9757–9763. doi:10.1039/c3ra41963k
  • Kiss, L.; Cherepanova, M.; Forró, E.; Fülöp, F. A New Access Route to Functionalized Cispentacins from Norbornene β‐Amino Acids. Chemistry (Weinheim an der Bergstrasse, Germany) 2012, 19, 2102–2107. doi:10.1002/chem.201203183
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