Metal-mediated aminocatalysis provides mild conditions: enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions

M Leven, JM Neudörfl…

Index: Leven, Matthias; Neudoerfl, Joerg M.; Goldfuss, Bernd Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 155 - 165

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Citation Number: 4

Abstract

Abstract Four catalysts based on new amides of chiral 1, 2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of 4-hydroxycoumarin to enones gives ee's up to 83% and almost quantitative yields in many cases. This novel type of catalysis provides an ...