Modular synthesis of non-conjugated N-(quinolin-8-yl) alkenyl amides via cross-metathesis.

We report a direct and modular method to access non-conjugated alkenyl amides containing the 8-aminoquinoline (AQ) directing auxiliary and related groups via cross-metathesis. In this way, readily available, AQ-containing, terminal β,γ-unsaturated amides can be coupled with various terminal alkenes to furnish internal alkene products that are otherwise difficult to prepare. The value of this family of products stems from their ability to participate in a number of directed alkene functionalization reactions.