Víctor Laserna, PhD student under the supervision of Prof. Arjan W. Kleij (ICIQ), has defended his PhD Thesis entitled “Small Molecule Activation for the Formation of Heterocyclic Compounds” (assigned to the Organic and Analytical Chemistry Department of the Universitat Rovira i Virgili) publicly on October 25th at the ICIQ Auditorium.
The members of the evaluation committee were: Prof. Marta Elena González (Universidad de Alcalá de Henares), Prof. Giulia Licini (Universidad de Padova) and Prof. Antonio Leandro Otero (Universidad de Castilla la Mancha)
Lewis acid catalyzed coupling reactions between epoxides and different heterocumulenes can lead to a wide variety of interesting heterocycles. Aluminium aminotriphenolates (ATP) have proven to be very active catalyst in the activation of epoxides towards the formation of cyclic carbonates via CO2 couplings, and we set out to explore further catalytic potential in the synthesis of other heterocyclic targets. Aminotriphenolate complexes are tunable and readily synthesized catalysts with great potential in Lewis acid catalysis. Using this type of Lewis acids (combined with halide cocatalysts), we have developed a series of straightforward and simple methodologies for the synthesis of oxazolidinones, cyclic sulfites, and cyclic carbonates with challenging substitution patterns. We have specially focused on the diastereoselectivity of the products, and have developed means to control it by identifying conditions which favour different intermediates in the reaction pathway. Finally we have investigated how this heterocycles can be useful synthons for the synthesis of other value added compounds.