Facile evolution of asymmetric organocatalysts in water assisted by surfactant Bronsted acids

Simple mixing of chiral amines and surfactant Bronsted acids such as p-dodecyl benzenesulfonic acid (DBSA) leads to highly effective and selective organocatalysts in water. The in situ generated catalysts catalyze highly stereoselective desymmetrization of prochiral ketones via direct aldol reactions (up to >16:1 dr, > 99% ee) in water using micelle as reaction media. The current strategy was also applied in asymmetric Michael addition leading to a catalytic system with good activity and stereoselectivity. (C) 2007 Elsevier Ltd. All rights reserved.