A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane

While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A tere...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2017-05, Vol.19 (9), p.2342-2345
Hauptverfasser:	Steemers, Luuk, Wanner, Martin J, Ehlers, Andreas W, Hiemstra, Henk, van Maarseveen, Jan H
Format:	Artikel
Sprache:	eng
Schlagworte:	chemical bonding chemical reactions Letter moieties organic compounds
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	2345
container_issue	9
container_start_page	2342
container_title	Organic letters
container_volume	19
creator	Steemers, Luuk Wanner, Martin J Ehlers, Andreas W Hiemstra, Henk van Maarseveen, Jan H
description	While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A terephthalic acid template core preorganizes the covalently connected ring precursor fragments to induce a clipping-type cyclization over the thread moiety. Cleavage of the temporary ester bonds that connect the ring and thread fragments liberates the [2]rotaxane.
doi_str_mv	10.1021/acs.orglett.7b00877
format	Article
fullrecord	<record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5423707</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1891891610</sourcerecordid><originalsourceid>FETCH-LOGICAL-a478t-8cac6b933b5500f4bc8d7773ddb2770d0b2a56fcc4479b11b01d787d6d5190af3</originalsourceid><addsrcrecordid>eNqFUV1LwzAUDaK4Of0FgvTRl243adO0IMIofsFA2PRJJCRpunV0zUy64f69GZtDXxQu5HJzzuGeexC6xNDHQPBAKNc3dlrrtu0zCZAydoS6mJIoZEDJ8aFPoIPOnJsDYD_JTlGHpHHEIKVddDMMJjNj2yA3a1Hrpg0mm6adaVe5wJSBaIJhXYe5sNI04bhqpsEbeR-bVnyKRp-jk1LUTl_s3x56vb97yR_D0fPDUz4chSJmaRumSqhEZlEkKQUoY6nSgjEWFYUkjEEBkgialErFMcskxhJwwVJWJAXFGYgy6qHbne5yJRe6UH5NK2q-tNVC2A03ouK_f5pqxqdmzWlMvE_mBa73AtZ8rLRr-aJySte1N2FWjhMg_nxxRON_oTjNtpVg8NBoB1XWOGd1edgIA99GxH1EfB8R30fkWVc_zRw435l4wGAH2LLnZmUbf9s_Jb8ABSufiw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1891891610</pqid></control><display><type>article</type><title>A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane</title><source>ACS Publications</source><creator>Steemers, Luuk ; Wanner, Martin J ; Ehlers, Andreas W ; Hiemstra, Henk ; van Maarseveen, Jan H</creator><creatorcontrib>Steemers, Luuk ; Wanner, Martin J ; Ehlers, Andreas W ; Hiemstra, Henk ; van Maarseveen, Jan H</creatorcontrib><description>While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A terephthalic acid template core preorganizes the covalently connected ring precursor fragments to induce a clipping-type cyclization over the thread moiety. Cleavage of the temporary ester bonds that connect the ring and thread fragments liberates the [2]rotaxane.</description><identifier>ISSN: 1523-7060</identifier><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.7b00877</identifier><identifier>PMID: 28437085</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>chemical bonding ; chemical reactions ; Letter ; moieties ; organic compounds</subject><ispartof>Organic letters, 2017-05, Vol.19 (9), p.2342-2345</ispartof><rights>Copyright © 2017 American Chemical Society</rights><rights>Copyright © 2017 American Chemical Society 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a478t-8cac6b933b5500f4bc8d7773ddb2770d0b2a56fcc4479b11b01d787d6d5190af3</citedby><cites>FETCH-LOGICAL-a478t-8cac6b933b5500f4bc8d7773ddb2770d0b2a56fcc4479b11b01d787d6d5190af3</cites><orcidid>0000-0002-1483-436X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b00877$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.7b00877$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28437085$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Steemers, Luuk</creatorcontrib><creatorcontrib>Wanner, Martin J</creatorcontrib><creatorcontrib>Ehlers, Andreas W</creatorcontrib><creatorcontrib>Hiemstra, Henk</creatorcontrib><creatorcontrib>van Maarseveen, Jan H</creatorcontrib><title>A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A terephthalic acid template core preorganizes the covalently connected ring precursor fragments to induce a clipping-type cyclization over the thread moiety. Cleavage of the temporary ester bonds that connect the ring and thread fragments liberates the [2]rotaxane.</description><subject>chemical bonding</subject><subject>chemical reactions</subject><subject>Letter</subject><subject>moieties</subject><subject>organic compounds</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUV1LwzAUDaK4Of0FgvTRl243adO0IMIofsFA2PRJJCRpunV0zUy64f69GZtDXxQu5HJzzuGeexC6xNDHQPBAKNc3dlrrtu0zCZAydoS6mJIoZEDJ8aFPoIPOnJsDYD_JTlGHpHHEIKVddDMMJjNj2yA3a1Hrpg0mm6adaVe5wJSBaIJhXYe5sNI04bhqpsEbeR-bVnyKRp-jk1LUTl_s3x56vb97yR_D0fPDUz4chSJmaRumSqhEZlEkKQUoY6nSgjEWFYUkjEEBkgialErFMcskxhJwwVJWJAXFGYgy6qHbne5yJRe6UH5NK2q-tNVC2A03ouK_f5pqxqdmzWlMvE_mBa73AtZ8rLRr-aJySte1N2FWjhMg_nxxRON_oTjNtpVg8NBoB1XWOGd1edgIA99GxH1EfB8R30fkWVc_zRw435l4wGAH2LLnZmUbf9s_Jb8ABSufiw</recordid><startdate>20170505</startdate><enddate>20170505</enddate><creator>Steemers, Luuk</creator><creator>Wanner, Martin J</creator><creator>Ehlers, Andreas W</creator><creator>Hiemstra, Henk</creator><creator>van Maarseveen, Jan H</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-1483-436X</orcidid></search><sort><creationdate>20170505</creationdate><title>A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane</title><author>Steemers, Luuk ; Wanner, Martin J ; Ehlers, Andreas W ; Hiemstra, Henk ; van Maarseveen, Jan H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a478t-8cac6b933b5500f4bc8d7773ddb2770d0b2a56fcc4479b11b01d787d6d5190af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>chemical bonding</topic><topic>chemical reactions</topic><topic>Letter</topic><topic>moieties</topic><topic>organic compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Steemers, Luuk</creatorcontrib><creatorcontrib>Wanner, Martin J</creatorcontrib><creatorcontrib>Ehlers, Andreas W</creatorcontrib><creatorcontrib>Hiemstra, Henk</creatorcontrib><creatorcontrib>van Maarseveen, Jan H</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Steemers, Luuk</au><au>Wanner, Martin J</au><au>Ehlers, Andreas W</au><au>Hiemstra, Henk</au><au>van Maarseveen, Jan H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2017-05-05</date><risdate>2017</risdate><volume>19</volume><issue>9</issue><spage>2342</spage><epage>2345</epage><pages>2342-2345</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>While the current supramolecular syntheses of [2]rotaxanes are generally efficient, the final product always retains the functional groups required for non-covalent preorganization. A short and high-yielding covalent-template-assisted approach is reported for the synthesis of a [2]rotaxane. A terephthalic acid template core preorganizes the covalently connected ring precursor fragments to induce a clipping-type cyclization over the thread moiety. Cleavage of the temporary ester bonds that connect the ring and thread fragments liberates the [2]rotaxane.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28437085</pmid><doi>10.1021/acs.orglett.7b00877</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-1483-436X</orcidid><oa>free_for_read</oa></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2017-05, Vol.19 (9), p.2342-2345
issn	1523-7060 1523-7052 1523-7052
language	eng
recordid	cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5423707
source	ACS Publications
subjects	chemical bonding chemical reactions Letter moieties organic compounds
title	A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T13%3A47%3A55IST&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=A%20Short%20Covalent%20Synthesis%20of%20an%20All-Carbon-Ring%20%5B2%5DRotaxane&rft.jtitle=Organic%20letters&rft.au=Steemers,%20Luuk&rft.date=2017-05-05&rft.volume=19&rft.issue=9&rft.spage=2342&rft.epage=2345&rft.pages=2342-2345&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.7b00877&rft_dat=%3Cproquest_pubme%3E1891891610%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=1891891610&rft_id=info:pmid/28437085&rfr_iscdi=true