Nitrogen-embedding heterocyclic nucleophiles in catalytic asymmetric vinylogous Mannich reactions

Abstract

the main objectives of this PhD program were focused on the development of the Mannich reaction in the vinylogous field. Intersecting the growing principles of asymmetric and organocatalysis, different protocols were developed: two for catalytic asymmetric vinylogous Mukaiyama-Mannich reaction with nitrogen-based silicon dienolates; they were successfully applied to aromatic and aliphatic aldimine donors. The ongoing project with 3-alkenyl-2-oxindoles as d4 donor progeny is also described: the final aim is the synthesis of 2,4-perhydro-alpha-carboline, natural and medicinal occurring scaffolds. A chapter is dedicated to the project in prof. Romo research gruop at texas A&M university: the development of a short, scalable and economical synthesis towards homobenzotetramisole and related organocatalysts.