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.
A three-component [3 + 2]-cycloaddition/elimination cascade for the synthesis of spirooxindole-pyrrolizines
Martina Palomba;Luana Bagnoli;Claudio Santi;Francesca Marini
2021
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.File in questo prodotto:
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