Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields and excellent enantio- and diastereoselectivities. The reaction conditions have been optimized by invoking ultrasonication and the influence of some structural moieties of the catalysts on the chemical yield and stereoselectivity of the Mannich products has been evaluated.
Efficient Catalysts for Asymmetric Mannich Reactions. -Chiral catalysts bearing stereogenic centers on the sulfinyl atom and on the carbon atoms in the chiral amine moiety are found to be highly efficient in the three component Mannich reaction of ketones aldehydes and amine (II). By modifying the catalyst it is shown, that the chiral amines have the largest influence on the stereochemical outcome of the reaction. -(RACHWALSKI*, M.; LEENDERS, T.; KACZMARCZYK, S.; KIELBASINSKI, P.; LESNIAK, S.; RUTJES, F. P. J. T.; Org. Biomol. Chem. 11 (2013) 25, 4207-4213, http://dx.doi.org/10.1039/c3ob40681d ; Inst. Mol. Mater., Radboud Univ. Nijmegen, NL-6525 ED Nijmegen, Neth.; Eng.) -S. Karsten 43-021
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