Chromatographically separable rotamers of an unhindered amide

Mario Geffe, Lars Andernach, Oliver Trapp and Till Opatz
Beilstein J. Org. Chem. 2014, 10, 701–706.

Supporting Information

Supporting Information File 1: Experimental procedures, HPLC chromatograms, copies of 1D and 2D NMR spectra of compounds 3 and 4, atom coordinates and DFT energies for ground- and transition states.
Format: PDF Size: 3.7 MB Download

Cite the Following Article

Chromatographically separable rotamers of an unhindered amide
Mario Geffe, Lars Andernach, Oliver Trapp and Till Opatz
Beilstein J. Org. Chem. 2014, 10, 701–706.

How to Cite

Geffe, M.; Andernach, L.; Trapp, O.; Opatz, T. Beilstein J. Org. Chem. 2014, 10, 701–706. doi:10.3762/bjoc.10.63

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Morris, D. T. J.; Wales, S. M.; Echavarren, J.; Žabka, M.; Marsico, G.; Ward, J. W.; Pridmore, N. E.; Clayden, J. Dynamic and Persistent Cyclochirality in Hydrogen-Bonded Derivatives of Medium-Ring Triamines. Journal of the American Chemical Society 2023, 145, 19030–19041. doi:10.1021/jacs.3c06570
  • Gawrys, P.; Morawski, O.; Banasiewicz, M.; Barboza, C. A. Magnifying the ESIPT process in tris(salicylideneanilines) via the steric effect - a pathway to the molecules with panchromatic fluorescence. Physical chemistry chemical physics : PCCP 2023, 25, 12500–12514. doi:10.1039/d3cp00638g
  • Niedzwiecka, A.; Pham, Q.; Ling, C.-C. Regiospecific O → N Acyl Migration as a Methodology to Access l-Altropyranosides with an N2,N4-Differentiation. Organic letters 2022, 24, 8667–8671. doi:10.1021/acs.orglett.2c03508
  • Chauthe, S. K.; Sidduri, P.; Reddy, M.; Sistla, R.; Byri, V.; Uttaravalli, M. D.; Botlagunta, M.; Kumar, H.; Gupta, A.; Gupta, A. K.; Bajpai, L.; Bagadi, M.; Mathur, A. RP-HPLC separation of interconvertible rotamers of a 5-tetrahydroisoquinolin-6-yl-pyridin-3-yl acetic acid derivative and confirmation by VT NMR and DFT study. Journal of pharmaceutical and biomedical analysis 2022, 212, 114675. doi:10.1016/j.jpba.2022.114675
  • Lv, J.; Li, Z.-H.; Deng, A.-J.; Qin, H.-L. A unified total synthesis of benzo[d][1,3]dioxole-type benzylisoquinoline alkaloids of aporphines, coptisines, and dibenzopyrrocolines. Organic & biomolecular chemistry 2022, 20, 658–666. doi:10.1039/d1ob02258j
  • Lewin, A. H.; Silinski, P. Handling and Analysis of 5-Formyl-, 5,10-Methenyl-, 10-Formyl-, 5-Formimno-, and 5,10-Methylenetetrahydrofolates. Methods in molecular biology (Clifton, N.J.) 2019, 1996, 75–94. doi:10.1007/978-1-4939-9488-5_8
  • Van Beek, W. E.; Weemaes, K.; Herrebout, W. A.; Velde, C. M. L. V.; Tehrani, K. A. Synthesis of 1-Aza-6,7-dehydrotropanes via Copper(I)-Catalyzed Coupling of 5-Chloropentan-2-one with Hydrazines and Terminal Alkynes. Synlett 2018, 29, 2643–2647. doi:10.1055/s-0037-1611041
  • Gamov, G. A.; Aleksandriiskii, V. V.; Sharnin, V. A. Inhibited rotation of amide group around CN bond of nicotinamide in different solvents by 1H NMR data. Journal of Molecular Liquids 2017, 231, 238–241. doi:10.1016/j.molliq.2017.01.078
  • Maddirala, A. R.; Andreana, P. R. Synthesis of 3-Substituted 2-Indol­inones by a Multicomponent Coupling Isocyanide-Dependent Microwave-Assisted Intramolecular Transamidation Process. European Journal of Organic Chemistry 2015, 2016, 196–209. doi:10.1002/ejoc.201501273
  • Walz, S.; Weis, S.; Franz, M.; Rominger, F.; Trapp, O. Investigation of the enantiomerization barriers of the phthalimidone derivatives EM12 and lenalidomide by dynamic electrokinetic chromatography. Electrophoresis 2015, 36, 796–804. doi:10.1002/elps.201400499
  • Čechová, L.; Procházková, E.; Císařová, I.; Dračínský, M.; Janeba, Z. Separation of planar rotamers through intramolecular hydrogen bonding in polysubstituted 5-nitrosopyrimidines. Chemical communications (Cambridge, England) 2014, 50, 14892–14895. doi:10.1039/c4cc06978a
  • Geffe, M.; Opatz, T. Enantioselective synthesis of (-)-dihydrocodeine and formal synthesis of (-)-thebaine, (-)-codeine, and (-)-morphine from a deprotonated α-aminonitrile. Organic letters 2014, 16, 5282–5285. doi:10.1021/ol5023849
Other Beilstein-Institut Open Science Activities