Herein we report the first asymmetric Michael reaction of arylidene-isoxazol-5-one with 1,3-diesters. Despite complex tautomer equilibria of the obtained Michael adducts, the one-pot entrapping strategy by the aid of different electrophiles/ protecting groups led to the selective isolation of diverse N-substituted isoxazol-5-ones in very high overall yield and good enan-Eur.the obtaining of isoindoline based heterocyclic compounds via organocatalytic cascade reactions. [22][23][24][25] Continuing our efforts aiming to develop challenging asymmetric synthesis of complex heterocyclic architectures of isoxazol-5-one, [15] considering the importance to perform sequential reactions in one-pot fashion for atom and step economy, [26] herein we describe the first enantioselective Michael reaction of malonate diesters with arylideneisoxazol-5-ones 1 and the selective tautomer entrapping of the respective adducts with electrophiles. Asymmetric three component Michael/electrophilic tautomer entrapping and four-component Knoevenagel/Michael/electrophilic-tautomer entrapping one-pot protocols have also been investigated and the results have been critically compared.