Hydroxy-α-amino acids modified by ionic liquid moieties: recoverable organocatalysts for asymmetric aldol reactions in the presence of water

New chiral ionic liquids bearing proline, serine or threonine moieties were synthesized. Compounds that contain 1-dodecylimidazolium or 4-(5-n-nonyl)-pyridinium cations and NTf₂ or PF₆ anions efficiently catalyze the asymmetric aldol reaction between aldehydes and ketones in the presence of water to generate aldols with high distereo- (up to 98:2) and enantioselectivity (up to >99% ee). 4-Hydroxyproline modified by the 4-(5-n-nonyl)-pyridinium hexafluorophosphate moiety retains its activity and selectivity over at least eight reaction cycles.