Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane.

The first chiral Lewis acid catalyzed enantioselective Friedel-Crafts alkylation of pyrroles with beta-CF(3) acrylates has been investigated, which afforded various types of chiral trifluoromethylated compounds in excellent yields (90-99%) with high ee's (up to 99% ee). With the aid of the Friedel-Crafts reaction adduct, optically active trifluorinated heliotridane was successfully constructed.