File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Dearomative Intramolecular (4+3) Cycloadditions of Thiophenes

TitleDearomative Intramolecular (4+3) Cycloadditions of Thiophenes
Authors
Zheng, YufenChen, YueyaoHe, YuxuanRizzo, AntonioZhou, YuchenLow, Kam HungKrenske, Elizabeth H.Chiu, Pauline
KeywordsCycloadditions
dearomatization’
density-functional calculations
desulfurization
thiophenes
Issue Date12-Aug-2024
PublisherJohn Wiley & Sons
Citation
Angewandte Chemie - International Edition, 2024, v. 63, n. 33 How to Cite?
DOI: http://dx.doi.org/10.1002/anie.202407059
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 Identifierhttp://hdl.handle.net/10722/354005
ISSN
1433-7851
2023 Impact Factor: 16.1
2023 SCImago Journal Rankings: 5.300
ISI Accession Number ID
WOS:001271183300001

 

DC FieldValueLanguage
dc.contributor.authorZheng, Yufen-
dc.contributor.authorChen, Yueyao-
dc.contributor.authorHe, Yuxuan-
dc.contributor.authorRizzo, Antonio-
dc.contributor.authorZhou, Yuchen-
dc.contributor.authorLow, Kam Hung-
dc.contributor.authorKrenske, Elizabeth H.-
dc.contributor.authorChiu, Pauline-
dc.date.accessioned2025-02-06T00:35:28Z-
dc.date.available2025-02-06T00:35:28Z-
dc.date.issued2024-08-12-
dc.identifier.citationAngewandte Chemie - International Edition, 2024, v. 63, n. 33-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://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.languageeng-
dc.publisherJohn Wiley & Sons-
dc.relation.ispartofAngewandte Chemie - International Edition-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.subjectCycloadditions-
dc.subjectdearomatization’-
dc.subjectdensity-functional calculations-
dc.subjectdesulfurization-
dc.subjectthiophenes-
dc.titleDearomative Intramolecular (4+3) Cycloadditions of Thiophenes-
dc.typeArticle-
dc.identifier.doi10.1002/anie.202407059-
dc.identifier.pmid38758985-
dc.identifier.scopuseid_2-s2.0-85198529367-
dc.identifier.volume63-
dc.identifier.issue33-
dc.identifier.eissn1521-3773-
dc.identifier.isiWOS:001271183300001-
dc.identifier.issnl1433-7851-

Export via OAI-PMH Interface in XML Formats

OR

Export to Other Non-XML Formats