Browsing Artículos by Author "Merino, Pedro"
Now showing items 1-10 of 10
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Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols
Capel, Estefanía; Rodríguez Rodríguez, Marta; Uria Pujana, Uxue ; Pedrón, José Manuel; Tejero, Tomás; Vicario Hernando, José Luis ; Merino, Pedro (American Chemical Society, 2021-12)[EN] The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with Nbromosuccinimide has been experimentally and computationally studied. The reaction ... -
Carboxylates as Nucleophiles in the Enantioselective Ring-Opening of Formylcyclopropanes under IminiumIon Catalysis
Díaz, Estibaliz; Reyes Martín, Efraim; Uria Pujana, Uxue ; Carrillo Fernández, María Luisa ; Tejero, Tomás; Merino, Pedro; Vicario Hernando, José Luis (Wiley-VCH, 2018-04-12)In this work, carboxylic acids, which are typically regarded as poor nucleophiles, are demonstrated to be competent reagents to promote the ring-opening of formylcyclopropanes after activation of the latter through iminium ... -
Catalytic Enantioselective Cloke–Wilson Rearrangement
Ortega Altonaga, Alesandere; Manzano, Rubén ; Uria Pujana, Uxue ; Carrillo Fernández, María Luisa ; Reyes Martín, Efraim; Tejero, Tomás; Merino, Pedro; Vicario Hernando, José Luis (Wiley-VCH, 2018-05-09)Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor ... -
Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
Rodríguez López, Sandra; Uria Pujana, Uxue ; Reyes Martín, Efraim; Carrillo Fernández, María Luisa ; Tejero, Tomás; Merino, Pedro; Vicario Hernando, José Luis (Wiley-VCH, 2020-02-10)The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the ... -
Mechanistic Insights in the Mode of Action of Bifunctional Pyrrolidine-Squaramide-derived Organocatalysts
Roca-López, David; Jørgensen, Karl Anker; Merino, Pedro; Uria Pujana, Uxue ; Reyes Martín, Efraim; Carrillo Fernández, María Luisa ; Vicario Hernando, José Luis (Wiley-VCH, 2016)The modes of catalytic action of three squaramide-derived bifunctional organocatalysts have been investigated using DFT methods. The [5+2] cycloaddition between oxidopyrilium ylides and enals has been used as model ... -
Organocatalytic Enantioselective Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement
Garay Goñi, Gorka; Hurtado, Josebe; Pedrón, José Manuel; García, Lorena; Reyes Martín, Efraim; Sánchez Díez, Eduardo; Tejero, Tomás; Carrillo Fernández, María Luisa ; Merino, Pedro; Vicario Hernando, José Luis (Wiley, 2023-05)We have demonstrated that the catalytic and enantioselective vinylcyclopropane-cyclopentene rearrangement can be carried out on (vinylcyclopropyl)acetaldehydes through activation via enamine intermediates. The reaction ... -
Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/ Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights
Orue Dañobeitia, Ane; Uria Pujana, Uxue ; Roca-López, David; Delso, Ignacio; Reyes Martín, Efraim; Carrillo Fernández, María Luisa ; Merino, Pedro; Vicario Hernando, José Luis (Royal Society of Chemistry, 2017-04-01)2-Hydroxydihydropyran-5-ones behave as excellent polyfunctional reagents able to react with enals through oxa-Michael/Michael process cascade under the combination of iminium and enamine catalysis. These racemic hemiacetalic ... -
Regioselectivity Change in the Organocatalytic Enantioselective (3+2) Cycloaddition with Nitrones Through Cooperative Hydrogen-Bonding Catalysis/Iminium Activation.
Prieto Aretxabaleta, Liher ; Juste-Navarro, Veronica; Uria Pujana, Uxue ; Delso, Ignacio; Reyes Martín, Efraim; Tejero, Tomás; Carrillo Fernández, María Luisa ; Merino, Pedro; Vicario Hernando, José Luis (Wiley-VCH, 2017-01-12)The reaction of nitrones with enals through iminium activation can be modulated by using cooperative hydrogen-bonding catalysis to induce the participation of a nitrone ylide (C-N-C) instead of the classical C-N-O dipole. ... -
Switchable Brønsted Acid-Catalyzed Ring Contraction of Cyclooctatetraene Oxide Towards the Enantioselective Synthesis of Cycloheptatrienyl-Substituted Homoallylic Alcohols and Oxaborinanes
Sendra, Jana; Salvadó Ruiz, Oriol; Pedrón, José Manuel; Reyes Martín, Efraim; Tejero, Tomás; Fernández Gutiérrez, Elena; Merino, Pedro; Vicario Hernando, José Luis (Wiley, 2023-04)The ability of cyclooctatetraene oxide to undergo two sequential ring contraction events under mild conditions, using Brønsted acid catalysis, has been studied in detail. We have found that the selectivity can be controlled ... -
The Pseudotransannular Ring Opening of 1-Aminocyclohept-4-ene-derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (+/-)-Ferrugine
Rodríguez López, Sandra; Uria Pujana, Uxue ; Reyes Martín, Efraim; Prieto Aretxabaleta, Liher ; Rodríguez Rodríguez, Marta; Tejero, Tomás; Merino, Pedro; Vicario Hernando, José Luis (Wiley, 2021-05-26)We have optimized a synthetic approach to (+/-)-Ferrugine in 8 steps starting from 5-aminocyclohept-1-ene and using the Bronsted acid-catalyzed pseudotransannular ring-opening of the epoxide derived from this cycloheptene ...