After optimizing the reaction conditions, we began exploring the scope of the organocascade reaction by varying of Nprotecting groups of methyleneindolinones 1 (Scheme 2A). We assessed the effect on reactivity and stereoselectivity of organocascade reactions using various N-protected methyleneindolinones. We identified oxycarbonyl-protecting groups as most effective in terms of stereocontrol; corresponding spirocyclic compounds 3a,b were isolated in good yields (43-60%) with high stereoselectivity. On the other hand, organocascade reactions of other N-protected methyleneindolinones did not give products with acceptable yields and stereochemical outcomes. For example, the organocascade reaction of unprotected methyleneindolinone 1f produced a mixture of products (3f/4f) with poor stereocontrol. Luckily, substrate 3f can be prepared in high yield by TFA-mediated deprotection of the N-Boc protecting group of 3a (for more details, please, see late-stage transformations). Subsequently, the scope of the developed organocascade reaction was investigated by varying substituted methyleneindolinones 1 (Scheme 2B). In general, spirooxindoles 3 were obtained in moderate-to-good yields with excellent stereoselectivity, when oxindole derivatives bearing electron-donating (3g, 3h) and weakly electronwithdrawing groups (3k-n) on the oxindole aromatic ring were used. The reaction of methyleneindolinones bearing a strong electron-withdrawing group, such as the nitro group, led to a complex mixture or to the decomposition of starting material. Additionally, we studied the process using variously substituted alkene of methyleneindolinone derivatives 1. Good efficiency of the developed method was shown in reactions of alkenes bearing various electron-withdrawing groups, especially in reactions of ester-derived alkenes producing spirocycles 3o-r in moderate-to-good yields (36-59%) and excellent stereochemical outcomes. Remarkably, other electron-withdrawing groups did not show similar efficiency. For example, the reaction between ketone-derived alkene 1t and 2a produced only elimination product 5t in moderate yield and low enantioselectivity. Scheme 2. The substrate scope of organocascade reaction.