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Among the three reagents selected as both rearrangement activators and F\n                    <jats:sub>3<\/jats:sub>\n                    CO\n                    <jats:sup>\u2013<\/jats:sup>\n                    anion sources, 2,4\u2010dinitro\u20101\u2010(trifluoromethoxy)benzene (DNTFB) was found to be the most effective. In each case, the OCF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010source was shown to play diverse key roles in the rearrangement. Enantioenriched trifluoromethoxy\u2010sulfoxides (up to 95% enantiomeric excess) were obtained using an oxaziridinium salt derived from cholesterol.\u00a0The configurational stability of these sulfoxides was investigated by thermal enantiomerization followed by enantioselective chromatography. Finally, the acidity of the protons in \u03b1\u2010position of the sulfinyl group was determined in DMSO (p\n                    <jats:italic>K<\/jats:italic>\n                    a value 20.3) suggesting the potency of this new scaffold for preparing trifluoromethoxylated trisubstituted C\u2010sp\n                    <jats:sup>3<\/jats:sup>\n                    centers via a deprotonation\/alkylation sequence.\n                  <\/jats:p>","DOI":"10.1002\/chem.202502465","type":"journal-article","created":{"date-parts":[[2025,11,20]],"date-time":"2025-11-20T07:29:21Z","timestamp":1763623761000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Intertwined Processes in the Pummerer\u2010Type Rearrangement Affording \u03b1\u2010Trifluoromethoxylated Thioethers and the Corresponding Highly Enantioenriched 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