1+1+3] Annulation of Diazoenals and Vinyl Azides: Direct Synthesis of Functionalized 1‐Pyrrolines through Olefination

Abstract

AbstractA dirhodium carboxylate catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides that gives synthetically important enal‐functionalized 1‐pyrroline derivatives was developed. The reaction involves a novel rhodium‐catalyzed olefination of diazoenals with vinyl azides via electrophilic enal carbenoids, resulting in a new class of enal acrylates. The annulation reaction was used for the direct synthesis of valuable deuterated 1‐pyrrolines. Structural diversification of the enal‐functionalized 1‐pyrrolines resulted in the biologically important pyrrolidine‐fused oxaziridine, amino acid derivatives, and a 6‐azabicyclo[3.2.1]octane motif present in polycyclic alkaloids.