Fernando and Isaac took part in the “European Researchers’ Night”

On 25 September, Isaac and Fernando took part in the “European Researchers’ Night” in Zaragoza. This is a huge international event that takes place in 280 cities across Europe and beyond, aiming to aproach Science to society.

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Scientific dissemination is an important and nice responsibility of the scientific community. Two young scientists of our HOCA research group proudly contributed to such effort  explaining two interesting topics to a very wide audience -from kids to adults-:

Isaac presented a virtual journey through the History of Chemistry telling brief stories and anecdotes of “Famous chemists in Organic Chemistry”.

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On the other hand, Fernando gave a talk approaching to his audience “The daily life of an organic chemist”.

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They both had a very and unique experience sharing their knowledge with many other city neighbours. HOCA wants to congratulate Isaac and Fernando for their effort, illusion and dedication in the “European Researchers’ Night” in Zaragoza.

 (Photos by R. P. Herrera)
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HOCA to publish a New Synthesis of Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridines)]

We are interested in the enantioselective synthesis of highly functionalized molecules with biological activity. In this frame, we have just published “a preliminary study” in the development of a “New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxo Spiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives”.

Fernando Auria-Luna, Eugenia Marqués-López, Somayeh Mohammadi, Roghayeh Heiran, Raquel P. Herrera. Molecules 2015, 20, 15807-15826. doi:10.3390/molecules200915807

Congratulations Fernando for this, your first article! Well done!
We keep nice memories of Somayeh and Somi, they worked really hard. Thanks girls!

 

Abstract: Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an grap abstractenamine with isatylidene malononitrile
derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%–58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited.

Keywords: chiral base; enamine; isatylidene malononitrile; 1,4-dihydropyridine; enantioselective; isatin; organocatalysis; spirooxindole; 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)]

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HOCA publishes a review about the synthesis of chromenes

We have compiled and reviewed the recent literature about “Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives” and the resulting article has been just published in Symmetry in the frame of its Special Issue dedicated to “Asymmetric Organocatalysis”.

Isaac G. Sonsona, Eugenia Marqués-López  and Raquel P. Herrera. Symmetry 2015, 7(3), 1519-1535; doi:10.3390/sym7031519

Congratulations guys for the well done job!

 

Abstract: The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis is a discipline in expansion that is already recognized as a well-established tool for obtaining enantiomerically enriched compounds. This review covers the particular case of the asymmetric synthesis of 2-amino-3-cyano-4H-chromenes using organocatalysis. Herein, we show the most symmetry-93392-graphicalillustrative examples of the methods developed by diverse research groups, following a classification based on these five different approaches: (1) addition of naphthol compounds to substituted α,α-dicyanoolefins; (2) addition of malononitrile to substituted o-vinylphenols; (3) addition of malononitrile to N-protected o-iminophenols; (4) Michael addition of nucleophiles to 2-iminochromene derivatives; and (5) organocatalyzed formal [4+2] cycloaddition reaction. In most cases, chiral thioureas have been found to be effective catalysts to promote the synthetic processes, and generally a bifunctional mode of action has been envisioned for them. In addition, squaramides and cinchona derivatives have been occasionally used as suitable catalysts for the substrates activation.

Keywords: chromene; benzopyran; 2-amino-3-cyano-4H-chromene; malononitrile; enantioselective; organocatalysis; synthesis; thiourea; squaramide; cinchona derivatives

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Isaac makes his debut as a scientific author!

Congratulations Isaac for your first paper! It looks fantastic!

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Isaac G. Sonsona. “Indole, a Privileged Structural Core Motif”. Synlett, 2015, DOI: 10.1055/s-0034-1381172.

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XXXV Biannual Congress of the RSEQ – A Coruña

Raquel has talked about “New Trends in Hydrogen Bonds Based Catalysts” in the XXXV Biannual Congress of the RSEQ that took place in A Coruña from 19th to 23rd July 2015.

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Raquel gave her talk, and…

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… enjoyed the beautiful city.

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Recognition of Research Groups of the Regional Government of Aragon

Our group has been registered as Grupo imagen BOA emergente de investigación (Emergent Research Group) by the Gobierno de Aragón (Regional Government of Aragon) under the name of  “Organocatálisis Asimétrica” (“Asymmetric Organocatalysis”).                      CONGRATULATIONS!

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7th Spanish-Portuguese-Japanese Organic Chemistry Symposium

Maru has been in Seville, coming back (for few days) to her alma mater university. Nice memories and nice time!

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Maru in front of her poster

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Closure

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Group picture

Thanks Charo, José María, Elena, David, Javi, Abel, and all the organizers!

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HOCA publishes a new method of addition of indoles to aliphatic β,γ-unsaturated α-ketoesters catalyzed by a chiral thiourea

Thiourea-Catalyzed Addition of Indoles to Aliphatic β,γ-Unsaturated α-Ketoesters” by Verónica Juste-Navarro, Eugenia Marqués-López and Raquel P. Herrera has been published in Asian Journal of Organic Chemistry.

DOI: 10.1002/ajoc.201500154

coverAbstract: The first thiourea-catalyzed addition reaction of indoles to aliphatic β,γ-unsaturated α-ketoesters has been developed. The easily accessible thiourea aminoindanol derivative makes this approach an interesting alternative for these aliphatic substrates, very scarcely employed in previously reported procedures, highlighting the complementarity of the strategy presented here. Final adducts, which are valuable intermediates for the obtainment of the corresponding α-amino acid or α-hydroxy acid derivatives, are obtained in good results under mild reaction conditions.

Keywords: asymmetric organocatalysis, indole, thiourea, aliphatic β,γ-unsaturated α-ketoester

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Wiley publica “Multicomponent reactions” editado por Herrera y Marqués-López

Multicomponent Reactions: Concepts and Applications for Design and Synthesis” es un libro editado por las investigadoras del grupo Organocatálisis asimétrica (H-OCA), Raquel P. Herrera y Eugenia Marqués-López, que ha sido publicado recientemente por Wiley.

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ISBN: 978-1-118-01600-8, publicado en abril de 2015

A lo largo de sus 532 páginas, un total de quince autores, todos ellos investigadores jóvenes del panorama internacional de científicos químicos realizan un minucioso estudio y puesta al día del tema tratado. En sus trece capítulos se exponen los métodos multicomponentes desarrollados desde el año 2005 abarcando todo tipo de reactividades, como puedan ser reacciones tipo Ugi, Biginelli, Passerini, Strecker, etc. Dos de los capítulos se dedican a las reacciones multicomponentes de naturaleza catalítica, uno abarca aquellos ejemplos en los que se emplea catálisis metálica y el otro organocatálisis. También se describen las aplicaciones de este tipo de estrategias en la obtención de fármacos, y otros compuestos de interés como pueden ser productos naturales.

Este libro será sin duda una herramienta esencial para los químicos cercanos a esta área de investigación. Y también será útil para toda la comunidad científica en general, así como para las industrias químicas. Esta recopilación exhaustiva, de la más amplia y actual forma de hacer química de manera eficiente mediante procesos de naturaleza multicomponente, podrá servir de inspiración tanto al mundo académico como al industrial para el desarrollo de sus futuras actuaciones.

Ahora puedes conseguir un 30% de descuento con este código: CHEM5

 

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“One-pot synthesis of unsymmetrical squaramides” just published in RCS Advances

Congratulations Juanvi for the recent publication of the “One-pot synthesis of unsymmetrical squaramides” in RCS Advances, 2015, 5, 33450-33462!

DOI: 10.1039/C5RA05383H

Abstract: The results concerning the first GA_One-pot synthesis SQUARAMIDESone-pot synthesis of unsymmetrical squaramides are reported. This straightforward procedure allows appealing and commonly used squaramide derivatives to be obtained with very good results. The methodology developed in this work saves energy, eliminates the purification steps for intermediate products, reduces costs and leads to better yields compared to those obtained through the traditional “stop-and-go” approach. Moreover, we have proved the efficiency of our process with the synthesis of three biologically active structures, improving the results of the previously reported stepwise syntheses. Interestingly, this simple and cheap method could attract the interest of pharmaceutical and chemical companies aiming to produce these active compounds on a large scale.

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