Research On Amino Acid Salt Catalyzed Asymmetric Michael Reaction Of 1,3-Dicarbonyls

Michael reaction is one of the most important types of reactions for the construction of C-C bond and chiral centre.As highly active prechiral substrates,1,3-dicarbonyl compounds are frequently employed in the asymmetric Michael addition reaction,which has been one of the hot topics of scientists.Thus,exploring new catalytic system for the asymmetric Michael addition of 1,3-dicarbonyl compounds is of great importance.In recent years,amino acid metal salts have been successfully applied in catalytic asymmetric organic reactions by us and other research groups.Based on previous studies of natural amino acids,we investigated their catalytic potential in the activation of 1,3-dicarbonyl compounds in thesis.We found barium(S)-prolinate can efficiently promote the reaction of acetylacetone with,maleic imide or 2-(2-oxoindolin-3-ylidene)malononitriles affording the succinimide and indole type spiro compounds,with excellent yield and moderate optical purity.The control experiment showed that the secondary amino group of barium(S)-proline played a key role in catalytic activity and enantioselectivity control.The unique organocatalysis lewis acid catalysis bifunctional catalytic mode of amino acid salts provides an efficient method for asymmetric transformations.This study provides a new idea for the asymmetric Michael reaction involving 1,3-dicarbonyl compounds,expands the application of amino acid salts in the field of asymmetric catalysis.