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Despite their importance, reactions that enable access to products precisely deuterated at an allylic position with complete control over the degree of deuteration are extremely rare. In fact, the high enantiopurity synthesis of enantioisotopomers owing their chirality solely to hydrogen isotopes at an allylic position has remained elusive to date. Herein, we report a modular Cu\u2010catalyzed semi\u2010reductive deuteration of allenes to access a broad scope of small molecules, drug analogs, and natural product analogs precisely deuterated at allylic positions. The semi\u2010reduction strategy has been applied to access a range of precisely labeled\n                    <jats:italic>d1<\/jats:italic>\n                    \u2010,\n                    <jats:italic>d2<\/jats:italic>\n                    \u2010,\n                    <jats:italic>d3<\/jats:italic>\n                    \u2010,\n                    <jats:italic>d5<\/jats:italic>\n                    \u2010, and\n                    <jats:italic>d7<\/jats:italic>\n                    \u2010isotopologs. In this work, we disclose the first high enantiopurity synthesis of allylic\u2010\n                    <jats:italic>d1<\/jats:italic>\n                    enantioisotopomers, along with a highly accurate and precise analysis for enantiomeric excess (EE) determination and assignment of absolute configuration (AC) using molecular rotational resonance (MRR) spectroscopy.\n                  <\/jats:p>","DOI":"10.1002\/anie.202525850","type":"journal-article","created":{"date-parts":[[2026,2,12]],"date-time":"2026-02-12T09:32:07Z","timestamp":1770888727000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Semi\u2010Reduction of Allenes to Access Deuterated Allylic Isotopomers, Isotopologs and Enantioisotopomers"],"prefix":"10.1002","volume":"65","author":[{"given":"Lihan","family":"Qi","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Tennessee  Knoxville Tennessee USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raviraj Ananda","family":"Thorat","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Tennessee  Knoxville Tennessee USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brad D.","family":"Maxwell","sequence":"additional","affiliation":[{"name":"Process Chemistry Vertex Pharmaceuticals Incorporated  Boston Massachusetts USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeffery A.","family":"Gladding","sequence":"additional","affiliation":[{"name":"Process Chemistry Vertex Pharmaceuticals Incorporated  Boston Massachusetts USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aniel J. 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