Base-Promoted Conversion of Propargylic Alcohols to 1,3-Enynes
Abstract
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.
Fields of Study & Subjects
Catalytic Alkyne Reactions
Organic Chemistry Synthesis Methods
Coordination Chemistry and Organometallics
Publication details
- Journal / source
- Organic Letters
- Volume
- 28
- Issue
- 7
- Pages
- 2500–2504
- Publication date
- 4 February 2026
- Language
- EN