Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecylsulfate (SDS) Upon a Three-Component Reaction of Aldehydes, Amines, and Ketones Under Neutral Conditions

A micellar solution of anionic, cationic or neutral surfactants can be used as an excellent medium for three-component Mannich reactions of aldehydes, amines, and ketones at room temperature. Sodium dodecylsulfate turned out to efficiently catalyze the reaction in neutral pure water (pH approximate to 7), and the corresponding desired beta-amino ketones precipitate while the reactions proceedes. This method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions, clean reaction profile, improved yields, and excellent regio- and diastereo-selectivities with a simple workup. Interesting examples of click chemistry under neutral conditions in water were observed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)