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- Publisher Website: 10.1002/anie.202407059
- Scopus: eid_2-s2.0-85198529367
- PMID: 38758985
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Article: Dearomative Intramolecular (4+3) Cycloadditions of Thiophenes
| Title | Dearomative Intramolecular (4+3) Cycloadditions of Thiophenes |
|---|---|
| Authors | |
| Keywords | Cycloadditions dearomatization’ density-functional calculations desulfurization thiophenes |
| Issue Date | 12-Aug-2024 |
| Publisher | John Wiley & Sons |
| Citation | Angewandte Chemie - International Edition, 2024, v. 63, n. 33 How to Cite? |
| Abstract | Unexpectedly facile dearomative intramolecular (4+3) cycloadditions of thiophenes with epoxy enolsilanes, providing sulfur-bridged cycloadducts, are reported. A total of fifteen thiophene substrates have been found to undergo (4+3) cycloaddition smoothly to produce endo and exo (4+3) adducts in yields of up to 83 % with moderate to good diastereoselectivity. Complete conservation of enantiomeric purity was observed when the optically enriched epoxide was used. The desulfurizing transformations of the sulfur-bridged skeleton of the cycloadducts provide functionalized 6,7-fused bicyclic frameworks consisting of 1,3-cycloheptadiene subunits. Density functional theory calculations reveal the origins of the facile dearomatization of thiophenes in these (4+3) cycloadditions. |
| Persistent Identifier | http://hdl.handle.net/10722/354005 |
| ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Zheng, Yufen | - |
| dc.contributor.author | Chen, Yueyao | - |
| dc.contributor.author | He, Yuxuan | - |
| dc.contributor.author | Rizzo, Antonio | - |
| dc.contributor.author | Zhou, Yuchen | - |
| dc.contributor.author | Low, Kam Hung | - |
| dc.contributor.author | Krenske, Elizabeth H. | - |
| dc.contributor.author | Chiu, Pauline | - |
| dc.date.accessioned | 2025-02-06T00:35:28Z | - |
| dc.date.available | 2025-02-06T00:35:28Z | - |
| dc.date.issued | 2024-08-12 | - |
| dc.identifier.citation | Angewandte Chemie - International Edition, 2024, v. 63, n. 33 | - |
| dc.identifier.issn | 1433-7851 | - |
| dc.identifier.uri | http://hdl.handle.net/10722/354005 | - |
| dc.description.abstract | <p>Unexpectedly facile dearomative intramolecular (4+3) cycloadditions of thiophenes with epoxy enolsilanes, providing sulfur-bridged cycloadducts, are reported. A total of fifteen thiophene substrates have been found to undergo (4+3) cycloaddition smoothly to produce endo and exo (4+3) adducts in yields of up to 83 % with moderate to good diastereoselectivity. Complete conservation of enantiomeric purity was observed when the optically enriched epoxide was used. The desulfurizing transformations of the sulfur-bridged skeleton of the cycloadducts provide functionalized 6,7-fused bicyclic frameworks consisting of 1,3-cycloheptadiene subunits. Density functional theory calculations reveal the origins of the facile dearomatization of thiophenes in these (4+3) cycloadditions.</p> | - |
| dc.language | eng | - |
| dc.publisher | John Wiley & Sons | - |
| dc.relation.ispartof | Angewandte Chemie - International Edition | - |
| dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
| dc.subject | Cycloadditions | - |
| dc.subject | dearomatization’ | - |
| dc.subject | density-functional calculations | - |
| dc.subject | desulfurization | - |
| dc.subject | thiophenes | - |
| dc.title | Dearomative Intramolecular (4+3) Cycloadditions of Thiophenes | - |
| dc.type | Article | - |
| dc.identifier.doi | 10.1002/anie.202407059 | - |
| dc.identifier.pmid | 38758985 | - |
| dc.identifier.scopus | eid_2-s2.0-85198529367 | - |
| dc.identifier.volume | 63 | - |
| dc.identifier.issue | 33 | - |
| dc.identifier.eissn | 1521-3773 | - |
| dc.identifier.issnl | 1433-7851 | - |