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The new ion\u2010paired reagent discovery was based upon the putative zwitterionic betaine intermediate of the Mitsunobu reaction and enabled the one\u2010step conversion of enantioenriched alcohols to valuable chiral C\u2212X bonds (where X=N, C, S, O or halide). The described activating reagent has also been applied to a one\u2010step methylation reaction using methanol and to an intermolecular amination\/intramolecular cyclization sequence that generates heterocycles, such as tetrahydroisoquinolines. This work provides the first evidence by X\u2010ray crystallography of a protonated betaine as intermediate in the Mitsunobu reaction.\n                  <\/jats:p>","DOI":"10.1002\/anie.202420312","type":"journal-article","created":{"date-parts":[[2025,2,10]],"date-time":"2025-02-10T23:24:55Z","timestamp":1739229895000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Universal Reagent for Mild and Stereospecific Nucleophilic Substitution of Alcohols with Amines"],"prefix":"10.1002","volume":"64","author":[{"given":"William S.","family":"Bechara","sequence":"first","affiliation":[{"name":"Universit\u00e9 de Montr\u00e9al FRQNT Centre in Green Chemistry and Catalysis Centre for Continuous Flow Synthesis Department of Chemistry  1375 av. 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