A three-component [3 + 2]-cycloaddition/elimination cascade for the synthesis of spirooxindole-pyrrolizines
Martina Palomba, Emanuela De Monte, Andrea Mambrini, Luana Bagnoli, Claudio Santi, Francesca Marini
Abstract
A three-component synthesis of novel spirooxindole-tetrahydropyrrolizines from secondary α-aminoacids, isatins and vinyl selenones has been disclosed. Products were formed in good yields and high diastereoselectivity by 1,3-dipolar cycloaddition of in situ generated azomethine ylides followed by spontaneous elimination of benzeneseleninic acid. Good regioselectivities with aryl substituted vinyl selenones were observed. The method showed good functional group tolerance, providing a direct approach to biologically relevant spirooxindoles under mild reaction conditions.
Topics & Concepts
CycloadditionCascadeComponent (thermodynamics)Combinatorial chemistryChemistryCascade reactionOrganic chemistryPhysicsCatalysisChromatographyThermodynamicsSynthesis and Characterization of PyrrolesOrganic Chemistry Cycloaddition ReactionsAsymmetric Synthesis and Catalysis