Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclo-propanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their a position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Automated summary

We present novel mild approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclo-propanes through Darzens inspired protocols. These anionic annulations, which have been rarely explored previously, yield products with appealing features that make them valuable building blocks for synthesis platforms. Specifically, trisubstituted acetophenone nucleophiles containing SCF3 and bromine substituents in their a position undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.