A new (S)-prolinamide modified by an ionic liquid moiety-a high performance recoverable catalyst for asymmetric aldol reactions in aqueous media

New prolinamide derivatives modified with ionic liquid moieties were synthesized and studied as organocatalysts in asymmetric aldol reactions in water. Aldol reactions between cycloalkanones or methylketones and aromatic aldehydes proceeded under studied conditions with high conversions (yields), diastereo- and enantioselectivities in the presence of a hydrophobic catalyst bearing a PF6 anion (1-5 mol%). The procedure is scalable and the catalyst retained its diastereo- and enantioselectivity over at least four reaction cycles and its activity over at least three reaction cycles. (C) 2009 Elsevier Ltd. All rights reserved.