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The origin of a transformation's stereoselectivity is one of the core issues in asymmetric catalysis. Herein, we propose a competitive induction model which is demonstrated to explore the origin of stereoselectivity for the Cu(I)/NHC‐catalysed [3+3] annulation. Computational studies reveal that chirality is jointly induced during a reversible nucleophilic addition, while the final stereochemical outcome is exclusively governed by the NHC organocatalyst in a subsequent irreversible step. More details are discussed in the article by Bai et al . on pages 508—516. image