Design and synthesis of fused-ring chiral ionic liquids from amino acid derivatives

Six novel imidazolium salts, which contain a chiral moiety as well as a fused-ring system, have been designed, synthesized, and fully characterized. The synthesis of these ionic liquids is concise and practical due to the commercial availability of the starting materials. These imidazolium compounds were readily prepared from 1-methyl-2-imidazoliumcarboxaldehyde and chiral amino alcohols. Salts that contain the PF₆ anion were solids, but salts with the NTf₂ anion were liquids at room temperature. We envision that these new chiral imidazolium compounds can serve as effective reaction media as well as chiral catalysts for asymmetric reactions, which are presently being investigated in our lab.