A Short Sequence for the Iterative Synthesis of Fused Polyethers
A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent...
Gespeichert in:
| Veröffentlicht in: | Helvetica chimica acta 2019-09, Vol.102 (9), p.n/a |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | n/a |
|---|---|
| container_issue | 9 |
| container_start_page | |
| container_title | Helvetica chimica acta |
| container_volume | 102 |
| creator | Elustondo, Frédéric Chintalapudi, Venkaiah Clark, J. Stephen |
| description | A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent ring formation by ring‐closing metathesis is present in the substrate but is masked in the form of a vinylic silane, which prevents competitive metathesis of the side chain. Generation of the reactive alkene from the unreactive vinylic silane is accomplished by hydroboration and subsequent acid‐mediated Peterson elimination of the intermediate hydroxysilane. |
| doi_str_mv | 10.1002/hlca.201900161 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2292089945</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2292089945</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2721-23c302d223d6e84de30d6bb7135879db9af8b5fa7ac6bfa093c2da1662d35ba03</originalsourceid><addsrcrecordid>eNqFkM1LAzEQxYMoWKtXzwHPWyeTbnZzsxT7AQWFKngL2XzQLWu3Jltl_3tTKnr0NPCb92Yej5BbBiMGgPebxugRApMATLAzMmA5YoaiyM_JILEyS7u3S3IV4xYApIRiQB4mdL1pQ0fX7uPgdsZR3wbabRxddi7orv50dN3vEoh1pK2ns0N0lj63Te8SDPGaXHjdRHfzM4fkdfb4Ml1kq6f5cjpZZQYLZBlywwEtIrfClWPrOFhRVQXjeVlIW0ntyyr3utBGVF6D5AatZkKg5XmlgQ_J3enuPrQpaezUtj2EXXqpECVCKeU4T6rRSWVCG2NwXu1D_a5DrxioY0vq2JL6bSkZ5MnwVTeu_0etFqvp5M_7DfXyat8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2292089945</pqid></control><display><type>article</type><title>A Short Sequence for the Iterative Synthesis of Fused Polyethers</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Elustondo, Frédéric ; Chintalapudi, Venkaiah ; Clark, J. Stephen</creator><creatorcontrib>Elustondo, Frédéric ; Chintalapudi, Venkaiah ; Clark, J. Stephen</creatorcontrib><description>A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent ring formation by ring‐closing metathesis is present in the substrate but is masked in the form of a vinylic silane, which prevents competitive metathesis of the side chain. Generation of the reactive alkene from the unreactive vinylic silane is accomplished by hydroboration and subsequent acid‐mediated Peterson elimination of the intermediate hydroxysilane.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.201900161</identifier><language>eng</language><publisher>Zürich: Wiley Subscription Services, Inc</publisher><subject>Ethers ; fused polyether ; Hydroboration ; latent alkene ; Metathesis ; Peterson elimination ; Polyethers ; ring-closing metathesis ; Substrates ; Synthesis</subject><ispartof>Helvetica chimica acta, 2019-09, Vol.102 (9), p.n/a</ispartof><rights>2019 The Authors. Published by Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2019 Wiley‐VHCA AG, Zurich, Switzerland</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2721-23c302d223d6e84de30d6bb7135879db9af8b5fa7ac6bfa093c2da1662d35ba03</cites><orcidid>0000-0003-1136-6932 ; 0000-0003-3935-0377</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fhlca.201900161$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.201900161$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Elustondo, Frédéric</creatorcontrib><creatorcontrib>Chintalapudi, Venkaiah</creatorcontrib><creatorcontrib>Clark, J. Stephen</creatorcontrib><title>A Short Sequence for the Iterative Synthesis of Fused Polyethers</title><title>Helvetica chimica acta</title><description>A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent ring formation by ring‐closing metathesis is present in the substrate but is masked in the form of a vinylic silane, which prevents competitive metathesis of the side chain. Generation of the reactive alkene from the unreactive vinylic silane is accomplished by hydroboration and subsequent acid‐mediated Peterson elimination of the intermediate hydroxysilane.</description><subject>Ethers</subject><subject>fused polyether</subject><subject>Hydroboration</subject><subject>latent alkene</subject><subject>Metathesis</subject><subject>Peterson elimination</subject><subject>Polyethers</subject><subject>ring-closing metathesis</subject><subject>Substrates</subject><subject>Synthesis</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkM1LAzEQxYMoWKtXzwHPWyeTbnZzsxT7AQWFKngL2XzQLWu3Jltl_3tTKnr0NPCb92Yej5BbBiMGgPebxugRApMATLAzMmA5YoaiyM_JILEyS7u3S3IV4xYApIRiQB4mdL1pQ0fX7uPgdsZR3wbabRxddi7orv50dN3vEoh1pK2ns0N0lj63Te8SDPGaXHjdRHfzM4fkdfb4Ml1kq6f5cjpZZQYLZBlywwEtIrfClWPrOFhRVQXjeVlIW0ntyyr3utBGVF6D5AatZkKg5XmlgQ_J3enuPrQpaezUtj2EXXqpECVCKeU4T6rRSWVCG2NwXu1D_a5DrxioY0vq2JL6bSkZ5MnwVTeu_0etFqvp5M_7DfXyat8</recordid><startdate>201909</startdate><enddate>201909</enddate><creator>Elustondo, Frédéric</creator><creator>Chintalapudi, Venkaiah</creator><creator>Clark, J. Stephen</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0003-1136-6932</orcidid><orcidid>https://orcid.org/0000-0003-3935-0377</orcidid></search><sort><creationdate>201909</creationdate><title>A Short Sequence for the Iterative Synthesis of Fused Polyethers</title><author>Elustondo, Frédéric ; Chintalapudi, Venkaiah ; Clark, J. Stephen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2721-23c302d223d6e84de30d6bb7135879db9af8b5fa7ac6bfa093c2da1662d35ba03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Ethers</topic><topic>fused polyether</topic><topic>Hydroboration</topic><topic>latent alkene</topic><topic>Metathesis</topic><topic>Peterson elimination</topic><topic>Polyethers</topic><topic>ring-closing metathesis</topic><topic>Substrates</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Elustondo, Frédéric</creatorcontrib><creatorcontrib>Chintalapudi, Venkaiah</creatorcontrib><creatorcontrib>Clark, J. Stephen</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Elustondo, Frédéric</au><au>Chintalapudi, Venkaiah</au><au>Clark, J. Stephen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Short Sequence for the Iterative Synthesis of Fused Polyethers</atitle><jtitle>Helvetica chimica acta</jtitle><date>2019-09</date><risdate>2019</risdate><volume>102</volume><issue>9</issue><epage>n/a</epage><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent ring formation by ring‐closing metathesis is present in the substrate but is masked in the form of a vinylic silane, which prevents competitive metathesis of the side chain. Generation of the reactive alkene from the unreactive vinylic silane is accomplished by hydroboration and subsequent acid‐mediated Peterson elimination of the intermediate hydroxysilane.</abstract><cop>Zürich</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/hlca.201900161</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0003-1136-6932</orcidid><orcidid>https://orcid.org/0000-0003-3935-0377</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0018-019X |
| ispartof | Helvetica chimica acta, 2019-09, Vol.102 (9), p.n/a |
| issn | 0018-019X 1522-2675 |
| language | eng |
| recordid | cdi_proquest_journals_2292089945 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Ethers fused polyether Hydroboration latent alkene Metathesis Peterson elimination Polyethers ring-closing metathesis Substrates Synthesis |
| title | A Short Sequence for the Iterative Synthesis of Fused Polyethers |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T16%3A47%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Short%20Sequence%20for%20the%20Iterative%20Synthesis%20of%20Fused%20Polyethers&rft.jtitle=Helvetica%20chimica%20acta&rft.au=Elustondo,%20Fr%C3%A9d%C3%A9ric&rft.date=2019-09&rft.volume=102&rft.issue=9&rft.epage=n/a&rft.issn=0018-019X&rft.eissn=1522-2675&rft_id=info:doi/10.1002/hlca.201900161&rft_dat=%3Cproquest_cross%3E2292089945%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2292089945&rft_id=info:pmid/&rfr_iscdi=true |