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Novel Photo- and Organo-catalytic Reactions for the Construction of C-C Bonds

Conferencia IIQ

Título: Novel Photo- and Organo-catalytic Reactions for the Construction of C-C Bonds

Conferenciante: Dr. José Alemán Lara (Universidad Autónoma de Madrid)

Fecha: viernes, 15 de febrero de 2019

Horario: 12:30 h

Lugar: Salón de Actos cicCartuja

 

Abstact

Photo-induced transformations have been at the forefront of chemical research for many years, yet lately they have received enormous interest. The basis for modern photocatalytic methodologies is set on the transmission of photons to a specific molecule - a photosensitizer, which can be parlayed into the population of the molecule’s excited state. This energy can then be transferred to other substrates via energy or electron transfer, wherein the pairing of excited-state energies and of redox potentials, respectively, of the sensitizer and the reactive substrate is crucial for a successful outcome in photochemical reactions. Very recently, our group has started a new research line concerning the use of photochemistry for different reactions, such as thiol-ene/oxidation tandem reactions,[1] asymmetric alkylation of aldehydes2 and ring opening cyclopropane expansions.3 More recently, we have found that the rupture of C-O bonds is possible and can be used for further transformations.

In the second part of this talk, I will present an approach for the asymmetric synthesis of tricyclic compounds, via desymmetrization of cyclohexadienones under aminocatalytic conditions.4 At the end of this communication, the use of bifunctional catalytic systems for the activation of silyl-dienol ethers for the synthesis of Rauhut-Currier type products will be presented.5. Finally, the use of different organocatalytic intramolecular activation with hydroxyl groups for the synthesis of pyrrolidines and aminoacids will be also shown.6 

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[1]. Guerrero-Corella, A.; Martinez, A. M.; Ahmadi, F.; Ming, E.; Fraile, A.; Alemán, J. Chem. Commun, 2017, 53, 10463.

2. Rigotti, T.; Casado-Sánchez, A.; Cabrera, S.; Pérez-Ruiz, R.; Liras, M.; A. de la Peña O'Shea, V.; Alemán, J. ACS-Catalysis, 2018, 8, 5928

3. Luis-Barrera, J.; Laina-Martín, V.; Rigotti, T.; Peccati, F.; Solans-Monfort, X.; Sodupe, M.; Mas-Ballesté, R.; Liras, M.; Alemán, J. Angew. Chem. Int. Ed. 2017, 56, 7826.

4. Martín-Santos, C.; Jarava-Barrera, C.; del Pozo, S.; Parra, A.; Díaz-Tendero, S.; Mas-Ballesté, R.; Cabrera, S.; Alemán, J. Angew. Chem. Int. Ed. 2014, 53, 8184.

5. Frias, M.; Mas-Ballesté, R.; Arias, S.; Alvarado, C.; Alemán, J. J. Am. Chem. Soc. 2017, 139, 672.

6. a) Esteban, F.; Cieślik, W.; Arpa, E. M.; Guerrero, A.;  Díaz Tendero, S.; Perles, J.; Fernández-Salas, J. A.;  Fraile, A.; Alemán, J. ACS-Catalysis, 2018, 8, 1884; b) Guerrero-Corella, A.; Esteban, F.; Iniesta, M.; Martín-Somer, A.; Parra, M.; Díaz-Tendero, S.; Fraile, A.; Alemán, J. Angew. Chem. Int. Ed. 2018,