A three-component [3 + 2]-cycloaddition/elimination cascade for the synthesis of spirooxindole-pyrrolizines
Martina Palomba1, Emanuela De Monte1, Andrea Mambrini1
1Department of Pharmaceutical Sciences (Group of Catalysis, Synthesis and Organic Green Chemistry), University of Perugia, Via del Liceo, 1 - 06123 Perugia, Italy. francesca.marini@unipg.it.
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.
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