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Herein, we report an enantioselective synthesis of compounds containing acyclic quaternary stereocenters through an iron\u2010catalyzed alkylation reaction between an acyclic tertiary alkyl source and an unactivated primary alkyl source. This method not only facilitates the rapid construction of sterically hindered motifs but also effectively enhances the saturation level of the molecule. Key to this method is an outer\u2010sphere C\u2500C bond formation mechanism, where enantioselectivity is governed by a cooperative triple catalysis system that combines photoredox, chiral Lewis acid, and iron catalysis. A series of compounds featuring acyclic quaternary stereocenters is produced under mild reaction conditions, and various transformations are presented to illustrate the potential applications of this approach. A comprehensive mechanistic study supports the crucial S\n                    <jats:sub>H<\/jats:sub>\n                    2 (bimolecular homolytic substitution) mechanism.\n                  <\/jats:p>","DOI":"10.1002\/anie.202506883","type":"journal-article","created":{"date-parts":[[2025,4,7]],"date-time":"2025-04-07T13:48:38Z","timestamp":1744033718000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Acyclic Quaternary Stereocenters via Catalytic Asymmetric Cross\u2010Couplings with Unactivated Alkyl\n                    <i>N<\/i>\n                    \u2010Hydroxyphthalimide Esters"],"prefix":"10.1002","volume":"64","author":[{"given":"Lian\u2010Jie","family":"Li","sequence":"first","affiliation":[{"name":"Shanghai Key Laboratory of Chemical Assessment and Sustainability School of Chemical Science and Engineering Tongji University  Shanghai 200092 P.R China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun\u2010Chun","family":"Zhang","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory of Chemical Assessment and Sustainability School of Chemical Science and Engineering Tongji University  Shanghai 200092 P.R China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia\u2010Yu","family":"Tang","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory of Chemical Assessment and Sustainability School of Chemical Science and Engineering Tongji University  Shanghai 200092 P.R China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hui","family":"Yu","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory of Chemical Assessment and Sustainability School of Chemical Science and Engineering Tongji University  Shanghai 200092 P.R China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ze\u2010Peng","family":"Yang","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory of Chemical Assessment and Sustainability School of Chemical Science and Engineering Tongji University  Shanghai 200092 P.R China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,4,17]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b00315"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00829"},{"key":"e_1_2_8_3_1","unstructured":"J. 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Notably a significant amount of the decarbonyl compound 2\u2010(5\u2010phenylpentyl)isoindoline\u20101 3\u2010dione is observed yielding 35% based on the NHP ester. Furthermore GC analysis indicates the presence of a small quantity of hydro\u2010dephthalimide product related to the NHP ester."},{"key":"e_1_2_8_112_1","unstructured":"Deposition number 2410484 (for3) contains the supplementary crystallographic data for this paper. 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