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Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecylsulfate (SDS) Upon a Three‐Component Reaction of Aldehydes, Amines, and Ketones Under Neutral Conditions
Author(s) -
Jafari Abbas Ali,
Moradgholi Fatemeh,
Tamaddon Fatemeh
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801037
Subject(s) - chemistry , mannich reaction , cationic polymerization , catalysis , component (thermodynamics) , sodium , organic chemistry , inorganic chemistry , physics , thermodynamics
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 ≈ 7), and the corresponding desired β‐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 diastereoselectivities with a simple workup. Interesting examples of click chemistry under neutral conditions in water were observed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)