A highly enantioselective tandem Michael addition of tryptamine‐derived oxindoles to alkynones was developed by taking advantage of a chiral N,N′‐dioxide Sc(OTf)3 catalyst. The reaction enables the facile preparation of enantioenriched spiropyrrolidine‐3,3′‐oxindole compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids (−)‐tubifoline, (−)‐tubifolidine, (−)‐dehydrotubifoline was achieved in 10–11 steps. Give me a ring: A novel method for synthesizing strychnos alkaloids was developed in which a chiral N,N′‐dioxide Sc(OTf)3 complex catalyzes the enantioselective tandem Michael addition of tryptamine‐derived oxindoles to alkynones. The reaction enables the facile preparation of enantioenriched spiropyrrolidine‐3,3′‐oxindole compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids.