Reactions of 3-benzylidene succinimides with 2-substituted 2-hydroxy-indane-1,3-diones and unsaturated pyrazolones are carried out under basic conditions to afford spirocyclized derivatives and Michael adducts, respectively, with high regio- and stereo-selectivities. The most notable aspect of the reaction is the ability of highly reactive benzylidene succinimide to act as both an electrophile and a nucleophile causing spirocyclization. The reaction proceeded under mild and metal-free conditions and products were isolated in good to high yields. The current strategy utilizes simple and easily accessible precursors, and provides functionally rich products of medicinal interest with two to four contiguous stereogenic centres and complete regioselectivity with excellent diastereoselectivity.