A novel organocatalytic asymmetric formal [3 + 2] cycloaddition of 3-substituted 1H-indoles with in situ generated 3-hydroxy-isoindolinone-derived β,γ-alkynyl-α-ketimines has been developed. A variety of biologically relevant chiral spiro-isoindolinone-indolines were achieved with excellent yields (up to 99%) and enantioselectivity (up to 99% ee) under mild conditions. The gram-scale reaction of this methodology and several interesting transformations of the products have been demonstrated.