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Reverse to success! A new formal [3+2] annulation reaction combining alkynyl aldehydes and β,γ‐unsaturated α‐ketoesters has been disclosed by using a NHC‐catalyzed/Lewis acid mediated strategy. This cooperative catalysis strategy first allows the “allenolate” intermediate as a nucleophilic synthon at the β‐position to react with activated electrophilic reagents by an addition reaction as the key CC...