Pd-Catalyzed Enantioselective [3+3] Annulation of Vinyldiazos with 2-Iodoanilines Enabled by Sadphos

Abstract

The use of aniline derivatives as 1,3-dipoles in Pd-catalyzed asymmetric [3+3] annulations, as well as the Pd-catalyzed asymmetric annulation of vinyldiazo compounds, remains underdeveloped. Herein, we report the first Pd-catalyzed asymmetric [3+3] annulation of 2-iodoanilines with vinyldiazo acetic esters. In this transformation, Ming-Phos exhibits uniquely high activity and enantioselectivity induction. The catalytic system accommodates a broad range of both coupling partners, affording a variety of enantioenriched dihydroquinolines in moderate to good yields.