Abstract
We have identified a switchable Prins cyclization process to form indoline-fused tetrahydrofurans and indole-fused oxepanes by applying different types of aldehydes under two sets of optimized conditions. Significantly, a novel Prins reaction mechanism involving an oxonium-mediated rearrangement in the formation of five-membered cyclic ethers is realized for the first time. (Figure presented.).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2620-2625 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 362 |
| Issue number | 13 |
| DOIs | |
| State | Published - Jul 16 2020 |
Keywords
- Prins cyclization
- aldehyde
- oxepane
- rearrangement
- tetrahydrofuran
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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CCDC 1975962: Experimental Crystal Structure Determination
Chen, X. (Contributor), Jiang, Y. (Contributor), Geng, H. (Contributor), Liu, X. (Contributor), Huang, Y. (Contributor), Lu, J. (Contributor), Gao, C. (Contributor), Zhang, S. (Contributor), Zhang, J. (Contributor) & Wang, W. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc24b4qc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc24b4qc&sid=DataCite
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