Fernando is now in Sitges attending to the “XXXVI Reunión Bienal de la Real Social Española de Química“. He has presented his talk about “Organocatalytic Synthesis of Chiral 1,4-Dihydropiridines”. Congratulations!
Asymmetric Organocatalytic Synthesis of Substituted Chiral 1,4-Dihydropyridine Derivatives. Fernando Auria-Luna, Eugenia Marqués-López, M. Concepción Gimeno, Roghayeh Heiran, Somayeh Mohammadi, and Raquel P. Herrera, J. Org. Chem. 2017, 82, 5516–5523.
Abstract. The first cinchona-alkaloid-organocatalyzed enantioselective synthesis of chiral 1,4-dihydropyridine derivatives is described. Bis-cinchona catalyst 3b activates the Michael addition reaction between malononitrile derivatives 2 and enamines 1, affording the appealing and highly substituted 1,4-dihydropyridines 4 with very good results in most cases. This is one of very few examples of the synthesis of chiral 1,4-dihydropyridines by an enantioselective catalytic procedure. The highly substituted final compounds are of interest for their potential biological activity. This efficient protocol opens the door to a new area of research for the asymmetric construction of these skeletons for which enantioselective syntheses are still very limited.
Our collaborator, Concepción Gimeno, awardee of the “IUPAC 2017 Distinguished Women in Chemistry or Chemical Engineering”
Last week, we celebrated Isaac’s birthday with a delicious cake that Sandra cooked for us.
Last friday Raquel and Javi enjoyed a football match in “La Romareda” supporting to Real Zaragoza (vs Cadiz CF).
Real Zaragoza scored first a goal, but finally the result was very frustrating (1-1). Next time!
Organocatalytic enantioselective synthesis of 1,4-dihydropyridines, Auria-Luna, F.; Marqués-López, E.; Herrera, R. P. Adv. Synth. Catal. 2017, DOI 10.1002/adsc.201700300
Abstract. This review aims to bring light upon a very interesting group of compounds, the 1,4-dihydropyridines (1,4-DHPs). These structures are well-known pharmacophores, used for many years to treat cardiovascular diseases because of their activity as calcium channel blockers. In addition, their potential as drugs to treat other affections has been recently exposed. The racemic synthesis of 1,4-DHPs has been well studied, while the asymmetric approaches are mainly based on the use of chiral auxiliaries or chiral resolutions. However, there are scarce examples regarding enantioselective organocatalytic methods. Herein, we will summarize the existing examples in this field of research.
Keywords. 1,4-dihydropyridine; 1,4–DHP; organocatalysis; (thio)urea; BINOL-derived phosphoric acid; aminocatalysis
Few weeks ago, we celebrated Raquel’s birthday. It was a nice party for a special number-40 😉
Direct Substitution of Alcohols in Pure Water by Brønsted Acid Catalysis. Ortiz, R.; Herrera, R. P. Molecules 2017, 22(4), 574; DOI:10.3390/molecules22040574.
This article belongs to the Special Issue Women in Organic Chemistry.
Abstract. With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. One process of particular interest is the direct nucleophilic substitution of an alcohol avoiding its preliminary transformation into a good leaving group, since one of the by-products in this approach would be water. The direct substitution of allylic, benzylic, and tertiary alcohols has been achieved through SN1-type reactions with catalytic amounts of Brønsted or Lewis acids; however, organic solvents are often required. In this review, the pioneering SN1 approaches performed in pure water and in the absence of a metal based Lewis acid are compiled and discussed.
Keywords: alcohol; non-catalyzed; organocatalysis; SN1; water