Development of Chiral 1,2,3-Triazolium Salts and Its Application for Catalytic Asymmetric Reactions

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Highly enantioselective chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been successfully developed by utilizing chiral 1,2,3-triazolium chlorides. The potential utility of the asymmetric halide ring-opening strategy has also been demonstrated by its application to the kinetic resolution of racemic, terminal aziridines. These catalytic asymmetricnucleophilic halogenations based on the use of trimethylsilyl halides rely on the ability of the appropriately modified, chiral 1,2,3-triazolium chloride to generate the requisite halosilicates and extend precise stereocontrol over the halide ion transfer.