biostudies-literatureUnknown28(7)Delattre M?cole Polytechnique F?d?rale de LausanneUnder acidic conditions, propargylic alcohols undergo Meyer-Schuster or Rupe rearrangements to afford two isomeric α,β-unsaturated ketones. Herein, we disclose a mechanistically distinct base-mediated regioselective conversion of TMS ethers of propargylic alcohols to 1,3-enynes in high yields with broad functional-group compatibility. Alternatively, trapping of the in situ-generated lithium acetylide with electrophiles enables access to functionalized internal 1,3-enynes. Owing to the ready accessibility of propargylic alcohols, this method provides a practical and attractive entry to synthetically valuable 1,3-enynes.Organic letters2500-2504https://www.ebi.ac.uk/biostudies/studies/S-EPMC12930487biostudies-literatureBase-Promoted Conversion of Propargylic Alcohols to 1,3-Enynes.PMC12930487Wiegand MDelattre MWang QZhu JfalseBase-Promoted Conversion of Propargylic Alcohols to 1,3-Enynes.Under acidic conditions, propargylic alcohols undergo Meyer-Schuster or Rupe rearrangements to afford two isomeric α,β-unsaturated ketones. Herein, we disclose a mechanistically distinct base-mediated regioselective conversion of TMS ethers of propargylic alcohols to 1,3-enynes in high yields with broad functional-group compatibility. Alternatively, trapping of the in situ-generated lithium acetylide with electrophiles enables access to functionalized internal 1,3-enynes. Owing to the ready accessibility of propargylic alcohols, this method provides a practical and attractive entry to synthetically valuable 1,3-enynes.2026-01-01T00:00:00Z2026 Feb2026-07-09T12:23:14.423Z2026-07-09T11:17:43.914ZS-EPMC129304874163891710.1021/acs.orglett.6c00196