Theoretical study of regioselectivity in the synthesis of spiro [pyrrolidine-2,3'-oxindole] compounds by [3+2] cycloaddition

摘要

Study of the structures of a series of spiro [pyrrolidine-2,3'-oxindole] derivatives synthesized by [3+2] cycloaddition reaction of isatin, alpha-amino acids, and beta-substituted phenylethylenes revealed the regioselectivity of the reaction was completely novel. The reaction mechanism for [3+2] cycloaddition of oxindole azomethine ylide and the beta-substituted phenylethylenes was calculated by use of density functional theory with the B3LYP functional and different basis sets. The results show that the regioselectivity of this [3+2] cycloaddition reaction is kinetically controlled, which agrees with experimental results.