Asymmetric synthesis is one of the most important areas of organic chemistry. The use of chiral solvents as the sole inducer of enantiomeric excess in organic reactions is a strategy that has been investigated previously. The difficult syntheses of chiral solvents and modest enantioselectivities often precluded their use. An attractive alternative to such solvents is chiral ionic liquids. Ionic liquids are nonvolatile, nonflammable materials with low or nonexistent melting points. Also, a significant transfer of chirality when used as a solvent in chemical synthesis can be expected due to their high degree of organization. This project focuses on developing efficient, economic and simple ways to prepare chiral ionic liquids. A series of pyrrolidinium-based chiral ionic liquids was prepared. The chirality was introduced by the lactate anion and the compounds were characterized by spectroscopic methods. The prepared chiral ionic liquids were then used in asymmetric Diels Alder reactions.

Synthesis and applications of chiral pyrrolidinium-based ionic liquids

247th National Meeting (2014)

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