# Base-Promoted Conversion of Propargylic Alcohols to 1,3-Enynes

## TL;DR

A new base-promoted method converts propargylic alcohols into 1,3-enynes with high efficiency and compatibility with various functional groups.

## Contribution

A novel base-mediated conversion of TMS ethers of propargylic alcohols to 1,3-enynes is introduced.

## Key findings

- Base-promoted conversion of TMS ethers of propargylic alcohols to 1,3-enynes occurs in high yields.
- The method is compatible with a broad range of functional groups.
- Lithium acetylide trapping with electrophiles provides access to functionalized internal 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.