Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Esteban P. Urriolabeitia, Pablo Sánchez, Alexandra Pop, Cristian Silvestru, Eduardo Laga, Ana I. Jiménez and Carlos Cativiela
Beilstein J. Org. Chem. 2020, 16, 1111–1123. https://doi.org/10.3762/bjoc.16.98

Supporting Information

Supporting Information File 1: Complete experimental section; copies of NMR spectra of 2 and 3.
Format: PDF Size: 7.2 MB Download
Supporting Information File 2: Copies on NMR spectra of compounds 4 and 5, crystallographic tables of compounds 2c and 4a.
Format: PDF Size: 5.3 MB Download

Cite the Following Article

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
Esteban P. Urriolabeitia, Pablo Sánchez, Alexandra Pop, Cristian Silvestru, Eduardo Laga, Ana I. Jiménez and Carlos Cativiela
Beilstein J. Org. Chem. 2020, 16, 1111–1123. https://doi.org/10.3762/bjoc.16.98

How to Cite

Urriolabeitia, E. P.; Sánchez, P.; Pop, A.; Silvestru, C.; Laga, E.; Jiménez, A. I.; Cativiela, C. Beilstein J. Org. Chem. 2020, 16, 1111–1123. doi:10.3762/bjoc.16.98

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.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 205.4 KB Download

Citations to This Article

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

Scholarly Works

  • Dalmau, D.; Crespo, O.; Matxain, J. M.; Urriolabeitia, E. P. Fluorescence Amplification of Unsaturated Oxazolones Using Palladium: Photophysical and Computational Studies. Inorganic chemistry 2023, 62, 9792–9806. doi:10.1021/acs.inorgchem.3c00601
  • Lin, J.; Lin, Q.; Zhu, L.; Xie, X.; Li, Y.; Li, L. Structural properties of Phoenix oolong tea polysaccharide conjugates and the interfacial stability in nanoemulsions. Journal of the science of food and agriculture 2023, 103, 5145–5155. doi:10.1002/jsfa.12583
  • Sierra, S.; López, R.; Gómez-Bengoa, E.; Falvello, L. R.; Urriolabeitia, E. P. Synthesis of 1,2-diaminotruxinic δ-cyclobutanes by BF3-controlled [2 + 2]-photocycloaddition of 5(4H)-oxazolones and stereoselective expansion of δ-cyclobutanes to give highly substituted pyrrolidine-2,5-dicarboxylates. Organic & biomolecular chemistry 2023, 21, 3203–3213. doi:10.1039/d3ob00284e
  • Martyanov, T. P.; Vorozhtsov, A. P.; Aleksandrova, N. A.; Sulimenkov, I. V.; Ushakov, E. N.; Gromov, S. P. Stereospecific Formation of the rctt Isomer of Bis-crown-Containing Cyclobutane upon [2 + 2] Photocycloaddition of an (18-Crown-6)stilbene Induced by Self-Assembly via Hydrogen Bonding. ACS omega 2022, 7, 42370–42376. doi:10.1021/acsomega.2c05295
  • Dalmau, D.; Jiménez, A. I.; Urriolabeitia, E. P. Synthesis and characterization of orthopalladated complexes containing tridentate C,N,O-oxazolones. Polyhedron 2022, 222, 115904. doi:10.1016/j.poly.2022.115904
  • Sierra, S.; Gomez, M. V.; Jiménez, A. I.; Pop, A.; Silvestru, C.; Marín, M. L.; Boscá, F.; Sastre, G.; Gómez-Bengoa, E.; Urriolabeitia, E. P. Stereoselective, Ruthenium-Photocatalyzed Synthesis of 1,2-Diaminotruxinic Bis-amino Acids from 4-Arylidene-5(4H)-oxazolones. The Journal of organic chemistry 2022, 87, 3529–3545. doi:10.1021/acs.joc.1c03092
  • Sierra, S.; Dalmau, D.; Higuera, S.; Cortés, D.; Crespo, O.; Jiménez, A. I.; Pop, A.; Silvestru, C.; Urriolabeitia, E. P. Reactivity of (Z)-4-Aryliden-5(4H)-thiazolones: [2 + 2]-Photocycloaddition, Ring-Opening Reactions, and Influence of the Lewis Acid BF3. The Journal of organic chemistry 2021, 86, 12119–12140. doi:10.1021/acs.joc.1c01458
  • Garcia-Sanz, C.; Andreu, A.; de las Rivas, B.; Jiménez, A. I.; Pop, A.; Silvestru, C.; Urriolabeitia, E. P.; Palomo, J. M. Pd-Oxazolone complexes conjugated to an engineered enzyme: improving fluorescence and catalytic properties. Organic & biomolecular chemistry 2021, 19, 2773–2783. doi:10.1039/d1ob00305d
  • Laga, E.; Dalmau, D.; Arregui, S.; Crespo, O.; Jiménez, A. I.; Pop, A.; Silvestru, C.; Urriolabeitia, E. P. Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization. Molecules (Basel, Switzerland) 2021, 26, 1238. doi:10.3390/molecules26051238
Other Beilstein-Institut Open Science Activities