Preparation of 4-Allenyloxazolines from (<i>Z</i>)-2-En-4-yn-1-ol via Propargyl/Allenyl Isomerization
A novel method for the preparation of 4-allenyl-oxazolines <b>2</b> is described via the reaction of 2-en-4-yn-1-ols <b>1</b> with trichloroacetonitrile in the presence of DBU. Reaction proceeds through the nucleophilic attack of OH functionality in <b>1</b> to CCl<sub>3</sub>CN followed by cyclization, propargyl/allene isomerization, and protonation. In this investigation, it is noticed that propargyl/allene isomerization is sensitive to the substituents.
Authors
- S. C. HUNG (ORCID: https://orcid.org/0009-0003-1387-8285)
- Shiuh‐Tzung Liu (ORCID: https://orcid.org/0000-0002-0544-006X)
- Yu‐Min Wang (ORCID: https://orcid.org/0000-0001-5182-8842)
- Yi‐Hung Liu (ORCID: https://orcid.org/0000-0003-3986-0086)
Institutions
- National Taiwan University (TW)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-23
- DOI
- https://doi.org/10.1021/acs.joc.4c01152
- Citations
- 1
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- National Science and Technology Council