Three-Component Synthesis of Di-Keto Aziridines and Highly Functionalized Alkenes from Sulfoxonium Ylides, Nitrosoarenes, and Alkynes.

Abstract

A catalyst-free one-pot three-component method of sulfoxonium ylides, nitrosoarenes, and alkynes for the synthesis of highly functionalized di-keto aziridines and alkenes is described. This strategy features the catalyst-free and additive-free approach, the employment of safe, more stable, and readily accessible sulfoxonium ylides, which bear a much wider substrate scope as starting materials. In terms of terminal alkynes, a cascade reaction of nitrone formation/1,3-diploar cycloaddition/Baldwin rearrangement is involved to afford a wide variety of di-keto aziridines. However, highly functionalized alkenes could be obtained instead of di-keto aziridines through the same nitrone formation/1,3-diploar cycloaddition and another different rearrangement reaction when internal alkynes are employed as starting materials.