Ortho-xylylene (o-xylylene) intermediates are highly reactive cis-dienes that have been exploited in numerous synthetic organic reactions to access novel compounds and develop new methodology. Due to their nature as cis-dienes, o-xylylenes are mostly used in cycloaddition reactions, like the Diels-Alder reaction, but have recently also been applied in nucleophilic additions. These intermediates have been generated from a wide range of precursors, but many of these methods require harsh conditions. The research presented in this thesis describes a mild method to generate o-xylylene intermediates from alkenyl aldimines. Following the formation of the reactive intermediate, a sufficient nucleophile is used to trap the o-xylylene. Additionally, this method provides access to tetrahydroisoquinoline derivatives, which are important motifs in natural products and bioactive molecules. This novel method broadens the scope of methods to generate o-xylylenes and their applications in nucleophilic additions.
