Abstract
Highly regioselective, 6-endo cyclization between propargyl alcohols and ambident enols such as naphthols, 4-hydroxy coumarin, cyclohexane-1,3-dione, 5,5-dimethylcyclohexane-1,3-dione is described using Ca(OTf)2 under solvent free conditions. The reaction proceeds through a cascade annulation which involves an etherification, Claisen type rearrangement, allene formation and endocyclization. Further, we extended this method to the synthesis of iodo-derivative and demonstrated the reactivity in cross-coupling reactions.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4642-4647 |
| Number of pages | 6 |
| Journal | Tetrahedron Letters |
| Volume | 58 |
| Issue number | 49 |
| DOIs | |
| State | Published - Dec 6 2017 |
| Externally published | Yes |
Bibliographical note
Publisher Copyright:© 2017 Elsevier Ltd
Keywords
- Ambident nucleophiles
- Benzochromenes
- Calcium catalysis
- Claisen rearrangement
- Propargyl alcohols
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