Ampliando el alcance estructural de la reacción 1,3-dipolar catalítica asimétrica de iluros de azometino: procesos intramoleculares y empleo de dipolos y dipolarófilos no convencionales

Resum

Pyrrolidine derivatives have attracted great attention in recent years owing to both their abundance in asymmetric synthesis. The catalytic asymmetric 1,3-dipolar cycloaddition between azomethine ylides and activated olefins is one of the most straightforward methods for the enantioselective preparation of proline derivatives, frecuent moiety in bioactive natural products and usefulness as chiral ligands and organocatalysts. In spite of the recently advances in this area, this reaction has some structural limitations in both the dipole and the dipolarophile partners, which have restrained the synthetic applicability of this methodology. In this context, the main aim of my thesis is to expand the scope of this methodology to less reactive substrates (dipoles and dipolarophiles). The success in this general goal would provide new methodologies for diversity-oriented syntheses of pyrrolidines with possible application in medicinal and material chemistry. This Doctoral Thesis is structured in five chapters: 1. Introduction 2. Catalytic asymmetric 1,3 dipolar cycloaddition of α heteroarylsilylimines and activated olefins 3. Catalytic asymmetric synthesis of azabicycles by 1,3 dipolar cycloaddition/intramolecular alkylation 4. Alkenylarenes as dipolarophiles in catalytic asymmetric 1,3 dipolar cycloadditions of azomethine ylides 5. Experimental section