Gold(I)-Catalyzed Functionalization of Pyrrole Derivatives: Stereoselective Synthesis of 7,8-Disubstituted 7,8-Dihydroindolizin-6(5H)-ones.

ABSTRACT

A gold-catalyzed cycloisomerization/nucleophilic addition/C-O rearrangement was developed starting from readily available pyrrole precursors. This efficient synthesis of 7,8-dihydroindolizin-6(5H)-ones (with the creation of new C-C and C-O bonds) allows access to key intermediates for the synthesis of natural and biologically active molecules. The functionalization process was independently optimized for both carbon and oxygen nucleophiles, and the versatility of this methodology was established by the synthesis of 36 different pyrrole derivatives (yields up to 90%).