Two Faces of Styrylsulfonium Salts: Domino Michael Addition/Cyclopropanation of 2-(2-Acylvinyl)indoles for the Synthesis of Cyclopropa[3,4]pyrrolo[1,2-a]indoles

Abstract

We report a domino reaction of 2-(2-acylvinyl)indoles as well as the corresponding pyrroles with styrylsulfonium salts under mild conditions, affording cyclopropamitosene analogues in high yields and complete diastereoselectivity. A wide range of (E)-β-hetaryl-α,β-unsaturated ketones were successfully employed for the synthesis of potentially bioactive cyclopropa[3,4]pyrrolo[1,2-a]indoles and related cyclopropa[a]pyrrolizines, demonstrating the versatility of the developed method. In contrast, (Z)-isomers of the substrates fail to give cyclopropamitosene derivatives but undergo cyclopropanation of the terminal methyl group.