Theoretical studies on the stereochemical course of 1,3-dipolar cycloaddition of azomethine ylides derived from indol-2,3-dione and thiazolidine-4-carboxylic acid

Abstract

1,3‐Dipolar cycloadditon of azomethine ylides with different dipolarophiles leads to the formation of novel heterocyclic spiro compounds having two or more chiral centers. The theoretical studies (HF/3–21G) on the 1,3‐dipolar cycloaddition reaction between ethene and azomethine ylide A4 derived from isatin and thaizolidine‐4‐carboxylic acid, indicates that the energy barrier for this addition is about ∼ 8 kcal/mol higher than that in simplest azomethine ylide A1. HF/3–21G studies on a series of azomethine ylides A2 and A3 suggested that the increased barrier is mainly due to stabilization of azomethine ylides arising from aromatic indol nucleus. Semi‐empirical studies indicate that the cycloaddition is streocontrolled as the transition states corresponding to only the stericlly allowed paths could be located on the potential energy surface.