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- Publisher Website: 10.1126/science.aau4821
- Scopus: eid_2-s2.0-85055911269
- PMID: 30385573
- WOS: WOS:000450460000041
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Article: Catalytic palladium-oxyallyl cycloaddition
Title | Catalytic palladium-oxyallyl cycloaddition |
---|---|
Authors | |
Issue Date | 2018 |
Citation | Science, 2018, v. 362, n. 6414, p. 564-568 How to Cite? |
Abstract | © 2017 The Authors. Exploration of intermediates that enable chemoselective cycloaddition reactions and expeditious construction of fused- or bridged-ring systems is a continuous challenge for organic synthesis. As an intermediate of interest, the oxyallyl cation has been harnessed to synthesize architectures containing seven-membered rings via (4+3) cycloaddition. However, its potential to access five-membered skeletons is underdeveloped, largely due to the thermally forbidden (3+2) pathway. Here, the combination of a tailored precursor and a Pd(0) catalyst generates a Pd-oxyallyl intermediate that cyclizes with conjugated dienes to produce a diverse array of tetrahydrofuran skeletons. The cycloaddition overrides conventional (4+3) selectivity by proceeding through a stepwise pathway involving a Pd-allyl transfer and ring closure sequence. Subsequent treatment of the (3+2) adducts with a palladium catalyst converts the heterocycles to the carbocyclic cyclopentanones. |
Persistent Identifier | http://hdl.handle.net/10722/276613 |
ISSN | 2023 Impact Factor: 44.7 2023 SCImago Journal Rankings: 11.902 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Trost, Barry M. | - |
dc.contributor.author | Huang, Zhongxing | - |
dc.contributor.author | Murhade, Ganesh M. | - |
dc.date.accessioned | 2019-09-18T08:34:08Z | - |
dc.date.available | 2019-09-18T08:34:08Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | Science, 2018, v. 362, n. 6414, p. 564-568 | - |
dc.identifier.issn | 0036-8075 | - |
dc.identifier.uri | http://hdl.handle.net/10722/276613 | - |
dc.description.abstract | © 2017 The Authors. Exploration of intermediates that enable chemoselective cycloaddition reactions and expeditious construction of fused- or bridged-ring systems is a continuous challenge for organic synthesis. As an intermediate of interest, the oxyallyl cation has been harnessed to synthesize architectures containing seven-membered rings via (4+3) cycloaddition. However, its potential to access five-membered skeletons is underdeveloped, largely due to the thermally forbidden (3+2) pathway. Here, the combination of a tailored precursor and a Pd(0) catalyst generates a Pd-oxyallyl intermediate that cyclizes with conjugated dienes to produce a diverse array of tetrahydrofuran skeletons. The cycloaddition overrides conventional (4+3) selectivity by proceeding through a stepwise pathway involving a Pd-allyl transfer and ring closure sequence. Subsequent treatment of the (3+2) adducts with a palladium catalyst converts the heterocycles to the carbocyclic cyclopentanones. | - |
dc.language | eng | - |
dc.relation.ispartof | Science | - |
dc.title | Catalytic palladium-oxyallyl cycloaddition | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1126/science.aau4821 | - |
dc.identifier.pmid | 30385573 | - |
dc.identifier.scopus | eid_2-s2.0-85055911269 | - |
dc.identifier.volume | 362 | - |
dc.identifier.issue | 6414 | - |
dc.identifier.spage | 564 | - |
dc.identifier.epage | 568 | - |
dc.identifier.eissn | 1095-9203 | - |
dc.identifier.isi | WOS:000450460000041 | - |
dc.identifier.issnl | 0036-8075 | - |