An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.
Yu, J. K., Chien, H. W., Lin, Y. J., Karanam, P., Chen, Y. H., & Lin, W. (2018). Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition. Chemical Communications, 54(71), 9921–9924. https://doi.org/10.1039/c8cc05693e