Ag(i)-catalyzed diastereoselective oxidative cyclopropanation of prochiral alkyne-tethered 1,3-dicarbonitriles†

Abstract

Herein, we developed a highly diastereoselective silver-catalyzed intramolecular cyclopropanation of prochiral alkyne-tethered 1,3-dicarbonitriles using perchloric acid as an effective oxidizing agent. This method facilitates the construction of densely functionalized complex [6.6.5.3] frameworks having three all-carbon quaternary stereocenters in high yields. The significance of the reaction was demonstrated by a gram-scale reaction and post-synthetic modifications of the product.