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Acetylene is a basic feedstock with a remarkable production over one million tons per year, although it is underutilized in the stereoselective synthesis of fine chemicals. Here we report a facile catalytic multicomponent reaction that allows for the enantio\u2010 and diastereoselective allylboration of acetylene gas. This process is catalyzed by a chiral copper catalyst, operates without specialized equipment or pressurization, and provides chiral skipped dienes bearing stereodefined and orthogonally functionalized olefins with excellent levels of chemo\u2010, regio\u2010, enantio\u2010 and diastereoselectivity. The combined stereochemical features and orthogonal functionalization make the products privileged structural scaffolds to access the complete set of stereoisomers of the chiral skipped diene core through simple enantio\u2010 and diastereodivergent pathways. The utility of the method is demonstrated with the enantioselective synthesis of three bioactive natural skipped diene products, namely (+)\u2010Nyasol, (+)\u2010Hinokiresinol and Phorbasin C, and other related synthetically relevant chiral molecules.<\/jats:p>","DOI":"10.1002\/anie.202407813","type":"journal-article","created":{"date-parts":[[2024,6,11]],"date-time":"2024-06-11T18:58:38Z","timestamp":1718132318000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Enantioselective Allylboration of Acetylene: A Versatile Tool for the Stereodivergent Synthesis of Natural Products"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8948-1258","authenticated-orcid":false,"given":"Andr\u00e9s M.","family":"\u00c1lvarez\u2010Constantino","sequence":"first","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e Materiais Moleculares (CiQUS) Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7216-2023","authenticated-orcid":false,"given":"Andrea","family":"Chaves\u2010Pouso","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e Materiais Moleculares (CiQUS) Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4903-0502","authenticated-orcid":false,"given":"Mart\u00edn","family":"Fa\u00f1an\u00e1s\u2010Mastral","sequence":"additional","affiliation":[{"name":"Centro Singular de Investigaci\u00f3n en Qu\u00edmica Biol\u00f3xica e Materiais Moleculares (CiQUS) Universidade de Santiago de Compostela  15782 Santiago de Compostela Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,7,24]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo1006812"},{"key":"e_1_2_8_2_1","unstructured":"P. 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