Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products. T...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2014-07, Vol.20 (28), p.8594-8598 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8598 |
|---|---|
| container_issue | 28 |
| container_start_page | 8594 |
| container_title | Chemistry : a European journal |
| container_volume | 20 |
| creator | Elbert, Bryony L. Lim, Diane S. W. Gudmundsson, Haraldur G. O'Hanlon, Jack A. Anderson, Edward A. |
| description | Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five‐membered cyclic siloxanes also couple under fluoride‐free conditions, whilst their six‐membered homologues do not, enabling orthogonality within this structural motif.
CycliZZZation! Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on a multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products (see scheme). |
| doi_str_mv | 10.1002/chem.201403255 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4531823</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3355521421</sourcerecordid><originalsourceid>FETCH-LOGICAL-c6095-e8c32ab6e6500f2d5651e63d85e5d0fc962ac282a3e3a1b30cb4f8674590bf9b3</originalsourceid><addsrcrecordid>eNqFkU1v1DAURS0EotPCliWyxKYsMvgjdmIWSKNQWlALqANCYmM5zkvHbRIPcVKaf49HM4wKm668eOcePb-L0AtK5pQQ9sauoJ0zQlPCmRCP0IwKRhOeSfEYzYhKs0QKrg7QYQjXhBAlOX-KDliaK8VSMkNuOXXDCoIL2Ne4mGzjLF40N9BNTXCNvzMdBFxOeAmtW01V76-gM4Pz3Vu8wMsBevBhDdbVMXfpxwHw4PHxz9fJToK_-maCKHmGntSmCfB89x6h7x9OvhVnyfmX04_F4jyxkiiRQG45M6UEKQipWSWkoCB5lQsQFamtksxYljPDgRtacmLLtM5llgpFylqV_Ai923rXY9lCZaEbetPode9a00_aG6f_nXRupa_8rU4FpznjUXC8E_T-1whh0K0LFpomnsKPQdMsy1S8LJcPoyJlTImcqIi--g-99mPfxUtsKMq5UjKL1HxL2d6H0EO935sSvSlcbwrX-8Jj4OX93-7xvw1HQG2B366B6QGdLs5OLu7Lk23WhQHu9lnT3-i4ayb0j8-n-uJ98Sljl6nO-R-kfMdq</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1541339967</pqid></control><display><type>article</type><title>Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Elbert, Bryony L. ; Lim, Diane S. W. ; Gudmundsson, Haraldur G. ; O'Hanlon, Jack A. ; Anderson, Edward A.</creator><creatorcontrib>Elbert, Bryony L. ; Lim, Diane S. W. ; Gudmundsson, Haraldur G. ; O'Hanlon, Jack A. ; Anderson, Edward A.</creatorcontrib><description>Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five‐membered cyclic siloxanes also couple under fluoride‐free conditions, whilst their six‐membered homologues do not, enabling orthogonality within this structural motif.
CycliZZZation! Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on a multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201403255</identifier><identifier>PMID: 24899240</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alkynes ; Biocompatibility ; Chemistry ; Communications ; cross-coupling ; hydrogenation ; Joining ; Natural products ; Orthogonality ; Rings (mathematics) ; Silanes ; Silicones ; Stereoselectivity ; Synthesis</subject><ispartof>Chemistry : a European journal, 2014-07, Vol.20 (28), p.8594-8598</ispartof><rights>2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</rights><rights>2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6095-e8c32ab6e6500f2d5651e63d85e5d0fc962ac282a3e3a1b30cb4f8674590bf9b3</citedby><cites>FETCH-LOGICAL-c6095-e8c32ab6e6500f2d5651e63d85e5d0fc962ac282a3e3a1b30cb4f8674590bf9b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201403255$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201403255$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24899240$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Elbert, Bryony L.</creatorcontrib><creatorcontrib>Lim, Diane S. W.</creatorcontrib><creatorcontrib>Gudmundsson, Haraldur G.</creatorcontrib><creatorcontrib>O'Hanlon, Jack A.</creatorcontrib><creatorcontrib>Anderson, Edward A.</creatorcontrib><title>Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five‐membered cyclic siloxanes also couple under fluoride‐free conditions, whilst their six‐membered homologues do not, enabling orthogonality within this structural motif.
CycliZZZation! Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on a multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products (see scheme).</description><subject>alkynes</subject><subject>Biocompatibility</subject><subject>Chemistry</subject><subject>Communications</subject><subject>cross-coupling</subject><subject>hydrogenation</subject><subject>Joining</subject><subject>Natural products</subject><subject>Orthogonality</subject><subject>Rings (mathematics)</subject><subject>Silanes</subject><subject>Silicones</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkU1v1DAURS0EotPCliWyxKYsMvgjdmIWSKNQWlALqANCYmM5zkvHbRIPcVKaf49HM4wKm668eOcePb-L0AtK5pQQ9sauoJ0zQlPCmRCP0IwKRhOeSfEYzYhKs0QKrg7QYQjXhBAlOX-KDliaK8VSMkNuOXXDCoIL2Ne4mGzjLF40N9BNTXCNvzMdBFxOeAmtW01V76-gM4Pz3Vu8wMsBevBhDdbVMXfpxwHw4PHxz9fJToK_-maCKHmGntSmCfB89x6h7x9OvhVnyfmX04_F4jyxkiiRQG45M6UEKQipWSWkoCB5lQsQFamtksxYljPDgRtacmLLtM5llgpFylqV_Ai923rXY9lCZaEbetPode9a00_aG6f_nXRupa_8rU4FpznjUXC8E_T-1whh0K0LFpomnsKPQdMsy1S8LJcPoyJlTImcqIi--g-99mPfxUtsKMq5UjKL1HxL2d6H0EO935sSvSlcbwrX-8Jj4OX93-7xvw1HQG2B366B6QGdLs5OLu7Lk23WhQHu9lnT3-i4ayb0j8-n-uJ98Sljl6nO-R-kfMdq</recordid><startdate>20140707</startdate><enddate>20140707</enddate><creator>Elbert, Bryony L.</creator><creator>Lim, Diane S. W.</creator><creator>Gudmundsson, Haraldur G.</creator><creator>O'Hanlon, Jack A.</creator><creator>Anderson, Edward A.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20140707</creationdate><title>Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes</title><author>Elbert, Bryony L. ; Lim, Diane S. W. ; Gudmundsson, Haraldur G. ; O'Hanlon, Jack A. ; Anderson, Edward A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6095-e8c32ab6e6500f2d5651e63d85e5d0fc962ac282a3e3a1b30cb4f8674590bf9b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>alkynes</topic><topic>Biocompatibility</topic><topic>Chemistry</topic><topic>Communications</topic><topic>cross-coupling</topic><topic>hydrogenation</topic><topic>Joining</topic><topic>Natural products</topic><topic>Orthogonality</topic><topic>Rings (mathematics)</topic><topic>Silanes</topic><topic>Silicones</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Elbert, Bryony L.</creatorcontrib><creatorcontrib>Lim, Diane S. W.</creatorcontrib><creatorcontrib>Gudmundsson, Haraldur G.</creatorcontrib><creatorcontrib>O'Hanlon, Jack A.</creatorcontrib><creatorcontrib>Anderson, Edward A.</creatorcontrib><collection>Istex</collection><collection>Wiley Online Library Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Elbert, Bryony L.</au><au>Lim, Diane S. W.</au><au>Gudmundsson, Haraldur G.</au><au>O'Hanlon, Jack A.</au><au>Anderson, Edward A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-07-07</date><risdate>2014</risdate><volume>20</volume><issue>28</issue><spage>8594</spage><epage>8598</epage><pages>8594-8598</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five‐membered cyclic siloxanes also couple under fluoride‐free conditions, whilst their six‐membered homologues do not, enabling orthogonality within this structural motif.
CycliZZZation! Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on a multigram scale, undergo Hiyama–Denmark coupling to give (Z)‐alkenyl polyene motifs found in bioactive natural products (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24899240</pmid><doi>10.1002/chem.201403255</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2014-07, Vol.20 (28), p.8594-8598 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4531823 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | alkynes Biocompatibility Chemistry Communications cross-coupling hydrogenation Joining Natural products Orthogonality Rings (mathematics) Silanes Silicones Stereoselectivity Synthesis |
| title | Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T04%3A47%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Cyclic%20Alkenylsiloxanes%20by%20Semihydrogenation:%20A%20Stereospecific%20Route%20to%20(Z)-Alkenyl%20Polyenes&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Elbert,%20Bryony%20L.&rft.date=2014-07-07&rft.volume=20&rft.issue=28&rft.spage=8594&rft.epage=8598&rft.pages=8594-8598&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201403255&rft_dat=%3Cproquest_pubme%3E3355521421%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1541339967&rft_id=info:pmid/24899240&rfr_iscdi=true |