From the structure of a series of spiro (pyrrolidine-2,3′-oxindole) derivatives synthesized by Huisgen reaction of isatin, α-amino acids, and different olefins, different regioselectivities were found. The possible mechanism of the Huisgen reaction of oxindole azomethine ylide and the substituent of olefins was investigated using a B3LYP/6-311G* level of theory, and the results show that the regioselection depends on the energy barrier between the stacking state and the regioisomer. This mechanism can also be applied to the illumination of other Huisgen reactions.
Research on Chemical Intermediates – Springer Journals
Published: Jul 3, 2012
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