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Herein we report an iterative boron\u2010homologation approach to construct various carbocycles from a single precursor. This method utilizes an electron\u2010withdrawing group (EWG) as a handle to enable intramolecular Matteson\u2010type couplings, leading to diastereoselective and enantioselective ring formation. An intriguing role of the Lewis acid additive is identified. This approach proves to be general for preparing carbocycles with different ring sizes and multiple stereocenters. The annulation processes are also scalable, and the products can undergo various transformations to provide synthetically valuable structural motifs. In addition, this method can be extended to the preparation of diverse hard\u2010to\u2010make spirocyclic compounds from simple cyclic ketones. Moreover, an iterative approach to synthesize double spirocycles is also demonstrated.<\/jats:p>","DOI":"10.1002\/anie.202503269","type":"journal-article","created":{"date-parts":[[2025,3,13]],"date-time":"2025-03-13T11:49:43Z","timestamp":1741866583000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Size\u2010Programmable Matteson\u2010Type Annulation: Construction of Spirocycles from Simple Cyclic Ketones"],"prefix":"10.1002","volume":"64","author":[{"given":"Woohyun","family":"Jo","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Chicago  Chicago IL 60637 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juliane K.","family":"Scholz","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Chicago  Chicago IL 60637 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