Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy
A templated backfolding concept to construct a [2]catenane was attempted via a quasi[1]catenane showing an inverted spiro geometry. The template is covalently connected to the ketal‐connected semi‐perpendicular‐arranged linear precursors and spatially directs the sterically congested backfolding mac...
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| Veröffentlicht in: | European journal of organic chemistry 2018-02, Vol.2018 (7), p.874-878 |
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| container_title | European journal of organic chemistry |
| container_volume | 2018 |
| creator | Steemers, Luuk Wanner, Martin J. van Leeuwen, Bart R. C. Hiemstra, Henk van Maarseveen, Jan H. |
| description | A templated backfolding concept to construct a [2]catenane was attempted via a quasi[1]catenane showing an inverted spiro geometry. The template is covalently connected to the ketal‐connected semi‐perpendicular‐arranged linear precursors and spatially directs the sterically congested backfolding macrocyclizations that are required to give a quasi[1]catenane. So far, we are unable to hydrolyze the cyclic ketal to liberate the [2]catenane.
A tartaric acid derived ketal‐centered quasi[1]catenane is prepared by a template‐directed covalent strategy forcing backfolding macrocyclizations. All key steps towards the quasi[1]catenane, i.e., macrolactonization, CuAAC macrocyclizations and RCM towards a cycloolefin, worked well. Unfortunately, all attempts to hydrolyze the ketal liberating the [2]catenane architecture failed. |
| doi_str_mv | 10.1002/ejoc.201701325 |
| format | Article |
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A tartaric acid derived ketal‐centered quasi[1]catenane is prepared by a template‐directed covalent strategy forcing backfolding macrocyclizations. All key steps towards the quasi[1]catenane, i.e., macrolactonization, CuAAC macrocyclizations and RCM towards a cycloolefin, worked well. Unfortunately, all attempts to hydrolyze the ketal liberating the [2]catenane architecture failed.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201701325</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Catenanes ; Spiro compounds ; Synthetic methods ; Templated synthesis</subject><ispartof>European journal of organic chemistry, 2018-02, Vol.2018 (7), p.874-878</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3575-50978bc9637505e936354949fa57c1d1c3534d1f68a887a817e7a4a95d9b534c3</citedby><cites>FETCH-LOGICAL-c3575-50978bc9637505e936354949fa57c1d1c3534d1f68a887a817e7a4a95d9b534c3</cites><orcidid>0000-0002-1483-436X ; 0000-0001-9514-3415</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%2Fejoc.201701325$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201701325$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Steemers, Luuk</creatorcontrib><creatorcontrib>Wanner, Martin J.</creatorcontrib><creatorcontrib>van Leeuwen, Bart R. C.</creatorcontrib><creatorcontrib>Hiemstra, Henk</creatorcontrib><creatorcontrib>van Maarseveen, Jan H.</creatorcontrib><title>Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy</title><title>European journal of organic chemistry</title><description>A templated backfolding concept to construct a [2]catenane was attempted via a quasi[1]catenane showing an inverted spiro geometry. The template is covalently connected to the ketal‐connected semi‐perpendicular‐arranged linear precursors and spatially directs the sterically congested backfolding macrocyclizations that are required to give a quasi[1]catenane. So far, we are unable to hydrolyze the cyclic ketal to liberate the [2]catenane.
A tartaric acid derived ketal‐centered quasi[1]catenane is prepared by a template‐directed covalent strategy forcing backfolding macrocyclizations. All key steps towards the quasi[1]catenane, i.e., macrolactonization, CuAAC macrocyclizations and RCM towards a cycloolefin, worked well. Unfortunately, all attempts to hydrolyze the ketal liberating the [2]catenane architecture failed.</description><subject>Catenanes</subject><subject>Spiro compounds</subject><subject>Synthetic methods</subject><subject>Templated synthesis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkN9LwzAQx4MoOKevPhd87rw0TdI8zjJ_MRjiBHGMkKXp7OzamWRK_3sz5o9Hn-64-3zu4IvQOYYBBkguzarVgwQwB0wSeoB6GISIgQk4DH1K0hgL8nyMTpxbAYBgDPfQy9B7s954U0SzZJ4rbxrVmOixa_yrcZWLPioVqehhq1w1w3P9Ayy6MJ0Gs1Y790rpt7Kti6pZRo_ehtmyO0VHpaqdOfuuffR0PZrmt_F4cnOXD8exJpTTmILg2UILRjgFagRhhKYiFaWiXOMCB4qkBS5ZprKMqwxzw1WqBC3EImw06aOL_d2Nbd-3xnm5are2CS9lAsDC1YwmgRrsKW1b56wp5cZWa2U7iUHu8pO7_ORvfkEQe-Gzqk33Dy1H95P8z_0Cg29zFA</recordid><startdate>20180221</startdate><enddate>20180221</enddate><creator>Steemers, Luuk</creator><creator>Wanner, Martin J.</creator><creator>van Leeuwen, Bart R. C.</creator><creator>Hiemstra, Henk</creator><creator>van Maarseveen, Jan H.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-1483-436X</orcidid><orcidid>https://orcid.org/0000-0001-9514-3415</orcidid></search><sort><creationdate>20180221</creationdate><title>Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy</title><author>Steemers, Luuk ; Wanner, Martin J. ; van Leeuwen, Bart R. C. ; Hiemstra, Henk ; van Maarseveen, Jan H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3575-50978bc9637505e936354949fa57c1d1c3534d1f68a887a817e7a4a95d9b534c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Catenanes</topic><topic>Spiro compounds</topic><topic>Synthetic methods</topic><topic>Templated synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Steemers, Luuk</creatorcontrib><creatorcontrib>Wanner, Martin J.</creatorcontrib><creatorcontrib>van Leeuwen, Bart R. C.</creatorcontrib><creatorcontrib>Hiemstra, Henk</creatorcontrib><creatorcontrib>van Maarseveen, Jan H.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Steemers, Luuk</au><au>Wanner, Martin J.</au><au>van Leeuwen, Bart R. C.</au><au>Hiemstra, Henk</au><au>van Maarseveen, Jan H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-02-21</date><risdate>2018</risdate><volume>2018</volume><issue>7</issue><spage>874</spage><epage>878</epage><pages>874-878</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A templated backfolding concept to construct a [2]catenane was attempted via a quasi[1]catenane showing an inverted spiro geometry. The template is covalently connected to the ketal‐connected semi‐perpendicular‐arranged linear precursors and spatially directs the sterically congested backfolding macrocyclizations that are required to give a quasi[1]catenane. So far, we are unable to hydrolyze the cyclic ketal to liberate the [2]catenane.
A tartaric acid derived ketal‐centered quasi[1]catenane is prepared by a template‐directed covalent strategy forcing backfolding macrocyclizations. All key steps towards the quasi[1]catenane, i.e., macrolactonization, CuAAC macrocyclizations and RCM towards a cycloolefin, worked well. Unfortunately, all attempts to hydrolyze the ketal liberating the [2]catenane architecture failed.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201701325</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1483-436X</orcidid><orcidid>https://orcid.org/0000-0001-9514-3415</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Catenanes Spiro compounds Synthetic methods Templated synthesis |
| title | Attempted [2]Catenane Synthesis via a Quasi[1]catenane by a Templated Backfolding Strategy |
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