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However, its reactivity as a nucleophile remains largely unexplored. Herein, we report an umpolung strategy that reverses the innate polarity of bicyclobutane aldehydes via N\u2010heterocyclic carbene (NHC) catalysis. This transformation enables the construction of novel rigidified lactones and lactams via coupling with diverse electrophilic partners, including aldehydes, ketones, and imines. The synthetic versatility of this method highlights its potential for applications in medicinal chemistry by providing new building blocks with defined exit vectors.<\/jats:p>","DOI":"10.1002\/anie.202513913","type":"journal-article","created":{"date-parts":[[2025,8,28]],"date-time":"2025-08-28T04:43:55Z","timestamp":1756356235000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Umpolung Activation of Bicyclobutanes via N\u2010Heterocyclic Carbene Catalysis"],"prefix":"10.1002","volume":"64","author":[{"given":"Yu\u2010Che","family":"Chang","sequence":"first","affiliation":[{"name":"Department of Chemistry Indiana University  800 E. Kirkwood Ave. Bloomington IN 47401 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renyu","family":"Guo","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indiana University  800 E. 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