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We report a one\u2010step, highly enantioselective and diastereoselective reductive protocol for the synthesis of oxa\u2010 and aza\u2010bicyclo[2.2.1]heptanes, enabled by [cobalt]\/[photoredox] (Co\/PC) catalysis. This methodology exploits heterobicyclic strained olefins as\n                    <jats:italic>\u03c0<\/jats:italic>\n                    \u2010coupling partners to directly access enantiomerically enriched bicyclo[2.2.1]heptanes from a wide range of alkynes, including terminal alkynes, propargylic alcohols, and internal alkynes. Mechanistic investigations, supported by DFT calculations, reveal that the oxidative coupling between the alkyne and alkene constitutes both the enantio\u2010 and rate\u2010determining step. DIPEA serves as an efficient electron\u2010donor, while the in situ\u2010generated secondary ammonium salt acts as a competent proton source.\n                  <\/jats:p>","DOI":"10.1002\/advs.202523407","type":"journal-article","created":{"date-parts":[[2026,6,26]],"date-time":"2026-06-26T12:56:13Z","timestamp":1782478573000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Cobalt\/Photoredox Catalyzed Desymmetrization of Oxo and Azabicycles via Asymmetric Reductive Coupling With Alkynes"],"prefix":"10.1002","volume":"13","author":[{"given":"Subhankar","family":"Pradhan","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Kanpur  Kanpur Uttar Pradesh India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arko","family":"Saha","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Kanpur  Kanpur Uttar 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