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Herein, we report a synergistic integration of electrocatalysis and asymmetric Lewis base catalysis that enables highly enantioselective radical functionalization of alkenes. This strategy centers on the anodic single\u2010electron oxidation of catalytically generated C1\u2010ammonium enolates\u2014derived from simple esters and chiral isothiourea organocatalysts\u2014to furnish chiral catalyst\u2010bound \u03b1\u2010acyl ammonium radical intermediates. Confined within the chiral cavity of the Lewis base catalyst, these tethered radicals undergo enantioselective addition to alkenes, and the resulting adduct radical is strategically diverted toward either difunctionalized or alkenylated products with high enantiocontrol (up to 99% ee). This work establishes a versatile platform that merges Lewis base catalysis with electrosynthesis for enantioselective alkene difunctionalization via direct ester C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2500H activation, thereby fundamentally extending the scope of asymmetric Lewis base organocatalysis into the realm of electrocatalytic radical transformations.\n                  <\/jats:p>","DOI":"10.1002\/anie.5599170","type":"journal-article","created":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T10:18:06Z","timestamp":1774606686000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Synergistic Lewis Base and Electrocatalysis for the Enantioselective Difunctionalization of Alkenes"],"prefix":"10.1002","volume":"65","author":[{"given":"Juan","family":"Li","sequence":"first","affiliation":[{"name":"Institutes of Physical Science and Information Technology Anhui University  Hefei China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiang","family":"Shan","sequence":"additional","affiliation":[{"name":"Institutes of Physical Science and Information Technology Anhui University  Hefei China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiqing","family":"Wang","sequence":"additional","affiliation":[{"name":"Institutes of Physical Science and Information Technology Anhui University  Hefei China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yong","family":"Liu","sequence":"additional","affiliation":[{"name":"Institutes of Physical Science and Information Technology Anhui University  Hefei China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0449-1727","authenticated-orcid":false,"given":"Jin","family":"Song","sequence":"additional","affiliation":[{"name":"Institutes of Physical Science and Information Technology Anhui University  Hefei 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