Host Research Group
ES38_Chemical synthesis and catalysis_Juan Miguel Oyarbide
Juan Miguel Oyarbide Garmendia
+34 943 015382
https://www.ehu.eus/es/web/gicas/hasiera
Group description
Our group is interested in the discovery and development of novel catalytic reactions for the asymmetric construction of new carbon-carbon and carbon-heteroatom bonds. These processes are crucial in areas such as the production of pharmaceutically active ingredients, agrochemical and fragrance industries, or advanced materials sciences.
The group consists of 4 permanent university professors and scientists, and hosts about half a dozen graduate students plus postdoctoral researchers. Our laboratories are equipped with state of the art instruments and facilities for organic synthesis, including high field NMR and HPLC. Techniques such as X-Ray, Elemental analysis, HRMS, etc. are also available on demand. The university library offers access to main scientific publications and databases.
Members of the group participate at several levels in research and teaching networks, inter alia, an inter-university Master degree program, an inter-department Doctoral program, specific collaboration at doctoral degree with University of Bordeaux, France, and permanent collaboration with Public University of Navarra at Pamplona.
The group main laboratory and facilities are located in the Faculty of Chemistry and the nearby buildings in the Donostia-San Sebastián university campus.
Keywords
- Organic synthesis
- Asymmetric catalysis
- Organocatalysis
- Synthetic methods
- Sustainable chemistry
- Bioactive compounds
Team Description
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Juan Miguel Oyarbide (Principle Investigator)
ORCID: 0000-0003-0362-0136
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José Ignacio Gamboa (Research staff)
ORCID: -
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Antonia Mielgo (Research staff)
ORCID: 0000-0001-8197-017X
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Aitor Landa (Research staff)
ORCID: 0000-0001-8574-8568
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Silvia Vera (Post-Doctoral researcher)
ORCID: 0000-0003-1670-4929
Projects
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Grupo de síntesis química y catálisis
Pl: JM Oyarbide
Funding Agency*: Regional
Ongoing: yes
Project reference: GIC21/41
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Catálisis asimétrica mediante bases de Bronsted para sustratos difíciles
Pl: C Palomo, JM Oyarbide
Funding Agency*: National
Ongoing: yes
Project reference: MINECOG19/P43
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Catálisis asimétrica y síntesis orgánica
Pl: JM Oyarbide
Funding Agency*: Regional
Ongoing: no
Project reference: GIC18/103
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Desarrollo de nuevos catalizadores y plantillas en organocatálisis asimétrica
Pl: C Palomo, JM Oyarbide
Funding Agency*: National
Ongoing: no
Project reference: MINECOG16/P40
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Catalizadores mono- y bifuncionales para transformaciones orgánicas asimétricas
Pl: C Palomo, JM Oyarbide
Funding Agency*: National
Ongoing: no
Project reference: MINECOG13/P48
Publications
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S. Vera, A. Vázquez, R. Rodriguez, S. del Pozo, I. Urruzuno, A. de Cózar, A. Mielgo, C. Palomo, = Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide, J. Org. Chem., 2021
10.1021/acs.joc.1c00406 -
O. Olaizola, I. Iriarte, G. Zanella, E. Gómez‐Bengoa, I. Ganboa, M. Oiarbide, C. Palomo, = Brønsted Base Catalyzed One‐Pot Synthesis of Stereodefined Six‐Member Carbocycles Featuring Transient Trienolates and a Key Intramolecular 1,6‐Addition, Angew. Chem. Int. Ed., 2019
10.1002/anie.201908693 -
J. Izquierdo, J. Etxabe, E. Duñabeitia, A. Landa, M. Oiarbide, C. Palomo, = Enantioselective Synthesis of 5,5-Disubstituted Hydantoins by Brønsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template, Chem. Eur. J., 2018
10.1002/chem.201800506 -
S. del Pozo, S. Vera, M. Oiarbide, C. Palomo, = Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids, J. Am. Chem. Soc., 2017
10.1021/jacs.7b09124 -
D. Bécart, V. Diemer, A. Salaün, M. Oiarbide, Y. R. Nelli, B. Kauffmann, L. Fischer, C. Palomo, G. Guichard, = Helical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C–C Bond-Forming Reactions, J. Am. Cem. Soc., 2017
10.1021/jacs.7b05802
Research Lines
ADVANCED MATERIALS AND PROCESSES
Asymmetric catalysis
Design and development of new catalysts and reagents (templates) useful for the development of atom- and step-economic chemical synthesis of densely functionalized organic molecules stereoselectively. Implementation of these methods into practical and sustainable routes to selected target compounds relevant to the bio-medicinal areas.
SUSTAINABLE MANUFACTURING
Asymmetric catalysis
Design and development of new catalysts and reagents (templates) useful for the development of atom- and step-economic chemical synthesis of densely functionalized organic molecules stereoselectively. Implementation of these methods into practical and sustainable routes to selected target compounds relevant to the bio-medicinal areas.
Several years ago the group started a collaboration with the group of Prof. Gilles Guichard at the Institute Européen de Chimie et de Biologie (IECB) and Université de Bordeaux aimed at exploring the potential of oligourea foldamers in chemical catalysis. As unique, highly ordered helical structures with strong hydrogen-bond network capabilities that may mimic small peptides, oligoureas constitute novel entities whose catalytic properties remain unexplored. Both understanding how they can work in activating organic substrates and reagents, and how to fully exploit their capabilities in asymmetric (organo)catalysis are our objectives. Up to now our joint efforts, which are financially supported by a collaborative ANR proposal (HCO_for_LLAC ANR-18-CE07-0018, along with D. Taton and P. Carbonière groups), have led to: one paper published (Bécart et al, J. Am. Chem. Soc. 2017, 139, 12524), two more in preparation (one with Prof. Daton, of the U. Bordeaux, dealing with new applications of some organocatalysts designed in our group to ring-opening polymerization processes), and two co-tutelle PhD Theses (D. Bécart 2018, A. Hacihasanoglu 2022).