Access to 1,2-dihydroisoquinolines through gold-catalyzed formal [4+2] cycloaddition

Abstract

A new synthetic route to the privileged 1,2-dihydroisoquinolines is reported. This method, which relies on a gold-catalyzed formal [4+2] cycloaddition between ynamides and imines, provides a new retrosynthetic disconnection of the 1,2-dihydroisoquinoline core by installing the 1,8a C-C and 2,3 C-N bonds in one step. Both aldimines and ketimines can be used as substrates. In addition, one example of dihydrofuropyridine synthesis is also demonstrated.

Keywords: cycloaddition; gold; heterocycles; homogeneous catalysis; ynamides.