1,1′-Bi(trishomobarrelenyl) - Synthesis and Chiroptic Properties
1,1′‐Bi(endo,exo,syn‐pentacyclo[3.3.3.02,4.06,8.09,11]undecyl)[1,1′‐bi(trishomobarrelenyl)] (4) has been prepared as a 1:1 mixture of its meso‐ and d,l‐diastereomers in six steps from trishomobarrelene 1 via the amine 5, the N,N′‐bis(trishomobarrelenyl)sulfamide 6 and the 1,2‐(trishomobarrelenyl)dia...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2009-03, Vol.2009 (7), p.1048-1052 |
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| container_title | European Journal of Organic Chemistry |
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| creator | de Meijere, Armin Rauch, Karsten Schrader, Bernhard Brackmann, Farina Pfoh, Roland Rühl, Stephan Katoh, Yasunaka Okamoto, Yoshio Wodrich, Matthew D. Corminboeuf, Clémence Schreiner, Peter R. |
| description | 1,1′‐Bi(endo,exo,syn‐pentacyclo[3.3.3.02,4.06,8.09,11]undecyl)[1,1′‐bi(trishomobarrelenyl)] (4) has been prepared as a 1:1 mixture of its meso‐ and d,l‐diastereomers in six steps from trishomobarrelene 1 via the amine 5, the N,N′‐bis(trishomobarrelenyl)sulfamide 6 and the 1,2‐(trishomobarrelenyl)diazene 7 in 16 % overall yield. Crystals of meso‐4 were grown from a pentane solution of the mixture and subjected to an X‐ray structure analysis. The (+)‐ and the (–)‐enantiomer were isolated by HPLC on a chiral‐phase column. They exhibited significantly enhanced molar optical rotations which are consistent with the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons. The absolute configuration of the (+)‐enantiomer was assigned on the basis of DFT computed optical rotations of both enantiomers to be all‐(S).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
(+)‐ And (–)‐1,1′‐bi(endo,exo,syn‐pentacyclo[3.3.02,4.06,8.09,11]undecyl) [1,1′‐bi(trishomobarrelenyl)], prepared along with the meso‐diastereomer, exhibit significantly enhanced molar optical rotations due to the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons. |
| doi_str_mv | 10.1002/ejoc.200801111 |
| format | Article |
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(+)‐ And (–)‐1,1′‐bi(endo,exo,syn‐pentacyclo[3.3.02,4.06,8.09,11]undecyl) [1,1′‐bi(trishomobarrelenyl)], prepared along with the meso‐diastereomer, exhibit significantly enhanced molar optical rotations due to the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200801111</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Chirality ; Density functional calculations ; Exact sciences and technology ; Helical structures ; Oligocyclic cyclopropane derivatives ; Organic chemistry ; Preparations and properties ; Small ring systems</subject><ispartof>European Journal of Organic Chemistry, 2009-03, Vol.2009 (7), p.1048-1052</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4231-64b6be0ed599c6362ae0e805144ed722a9907ad9d01273eae542a623ed0adf643</citedby><cites>FETCH-LOGICAL-c4231-64b6be0ed599c6362ae0e805144ed722a9907ad9d01273eae542a623ed0adf643</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%2Fejoc.200801111$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200801111$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,776,780,788,1411,27899,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21230486$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>de Meijere, Armin</creatorcontrib><creatorcontrib>Rauch, Karsten</creatorcontrib><creatorcontrib>Schrader, Bernhard</creatorcontrib><creatorcontrib>Brackmann, Farina</creatorcontrib><creatorcontrib>Pfoh, Roland</creatorcontrib><creatorcontrib>Rühl, Stephan</creatorcontrib><creatorcontrib>Katoh, Yasunaka</creatorcontrib><creatorcontrib>Okamoto, Yoshio</creatorcontrib><creatorcontrib>Wodrich, Matthew D.</creatorcontrib><creatorcontrib>Corminboeuf, Clémence</creatorcontrib><creatorcontrib>Schreiner, Peter R.</creatorcontrib><title>1,1′-Bi(trishomobarrelenyl) - Synthesis and Chiroptic Properties</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>1,1′‐Bi(endo,exo,syn‐pentacyclo[3.3.3.02,4.06,8.09,11]undecyl)[1,1′‐bi(trishomobarrelenyl)] (4) has been prepared as a 1:1 mixture of its meso‐ and d,l‐diastereomers in six steps from trishomobarrelene 1 via the amine 5, the N,N′‐bis(trishomobarrelenyl)sulfamide 6 and the 1,2‐(trishomobarrelenyl)diazene 7 in 16 % overall yield. Crystals of meso‐4 were grown from a pentane solution of the mixture and subjected to an X‐ray structure analysis. The (+)‐ and the (–)‐enantiomer were isolated by HPLC on a chiral‐phase column. They exhibited significantly enhanced molar optical rotations which are consistent with the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons. The absolute configuration of the (+)‐enantiomer was assigned on the basis of DFT computed optical rotations of both enantiomers to be all‐(S).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
(+)‐ And (–)‐1,1′‐bi(endo,exo,syn‐pentacyclo[3.3.02,4.06,8.09,11]undecyl) [1,1′‐bi(trishomobarrelenyl)], prepared along with the meso‐diastereomer, exhibit significantly enhanced molar optical rotations due to the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Chirality</subject><subject>Density functional calculations</subject><subject>Exact sciences and technology</subject><subject>Helical structures</subject><subject>Oligocyclic cyclopropane derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Small ring systems</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhQdRsFa3rrMRFJx65yeTztKGWn-KFVNR3AzTZEqnpkmZCWh2PpOP5JOYEinuvJtzL5zvXDgIHRPoEQB6YZZl2qMAfSDN7KAOASkxCAm7zc4Zx0Syl3104P0SAKQQpIMG5Jx8f37hgT2tnPWLclXOtHMmN0WdnwU4SOqiWhhvfaCLLIgX1pXryqbBQ6PGVdb4Q7Q317k3R7_aRU9Xw2l8jceT0U18OcYpp4xgwWdiZsBkoZSpYILq5uhDSDg3WUSplhIinckMCI2Y0SbkVAvKTAY6mwvOuqjX5qau9N6ZuVo7u9KuVgTUpgG1aUBtG2iAkxZYa5_qfO50kVq_pSihDHhfND7Z-t5tbup_UtXwdhL__YFb1vrKfGxZ7d6UiFgUquf7kUqmj0nyescUZz9HB3wb</recordid><startdate>200903</startdate><enddate>200903</enddate><creator>de Meijere, Armin</creator><creator>Rauch, Karsten</creator><creator>Schrader, Bernhard</creator><creator>Brackmann, Farina</creator><creator>Pfoh, Roland</creator><creator>Rühl, Stephan</creator><creator>Katoh, Yasunaka</creator><creator>Okamoto, Yoshio</creator><creator>Wodrich, Matthew D.</creator><creator>Corminboeuf, Clémence</creator><creator>Schreiner, Peter R.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200903</creationdate><title>1,1′-Bi(trishomobarrelenyl) - Synthesis and Chiroptic Properties</title><author>de Meijere, Armin ; Rauch, Karsten ; Schrader, Bernhard ; Brackmann, Farina ; Pfoh, Roland ; Rühl, Stephan ; Katoh, Yasunaka ; Okamoto, Yoshio ; Wodrich, Matthew D. ; Corminboeuf, Clémence ; Schreiner, Peter R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4231-64b6be0ed599c6362ae0e805144ed722a9907ad9d01273eae542a623ed0adf643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Chirality</topic><topic>Density functional calculations</topic><topic>Exact sciences and technology</topic><topic>Helical structures</topic><topic>Oligocyclic cyclopropane derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Small ring systems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>de Meijere, Armin</creatorcontrib><creatorcontrib>Rauch, Karsten</creatorcontrib><creatorcontrib>Schrader, Bernhard</creatorcontrib><creatorcontrib>Brackmann, Farina</creatorcontrib><creatorcontrib>Pfoh, Roland</creatorcontrib><creatorcontrib>Rühl, Stephan</creatorcontrib><creatorcontrib>Katoh, Yasunaka</creatorcontrib><creatorcontrib>Okamoto, Yoshio</creatorcontrib><creatorcontrib>Wodrich, Matthew D.</creatorcontrib><creatorcontrib>Corminboeuf, Clémence</creatorcontrib><creatorcontrib>Schreiner, Peter R.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>de Meijere, Armin</au><au>Rauch, Karsten</au><au>Schrader, Bernhard</au><au>Brackmann, Farina</au><au>Pfoh, Roland</au><au>Rühl, Stephan</au><au>Katoh, Yasunaka</au><au>Okamoto, Yoshio</au><au>Wodrich, Matthew D.</au><au>Corminboeuf, Clémence</au><au>Schreiner, Peter R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1,1′-Bi(trishomobarrelenyl) - Synthesis and Chiroptic Properties</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2009-03</date><risdate>2009</risdate><volume>2009</volume><issue>7</issue><spage>1048</spage><epage>1052</epage><pages>1048-1052</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>1,1′‐Bi(endo,exo,syn‐pentacyclo[3.3.3.02,4.06,8.09,11]undecyl)[1,1′‐bi(trishomobarrelenyl)] (4) has been prepared as a 1:1 mixture of its meso‐ and d,l‐diastereomers in six steps from trishomobarrelene 1 via the amine 5, the N,N′‐bis(trishomobarrelenyl)sulfamide 6 and the 1,2‐(trishomobarrelenyl)diazene 7 in 16 % overall yield. Crystals of meso‐4 were grown from a pentane solution of the mixture and subjected to an X‐ray structure analysis. The (+)‐ and the (–)‐enantiomer were isolated by HPLC on a chiral‐phase column. They exhibited significantly enhanced molar optical rotations which are consistent with the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons. The absolute configuration of the (+)‐enantiomer was assigned on the basis of DFT computed optical rotations of both enantiomers to be all‐(S).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
(+)‐ And (–)‐1,1′‐bi(endo,exo,syn‐pentacyclo[3.3.02,4.06,8.09,11]undecyl) [1,1′‐bi(trishomobarrelenyl)], prepared along with the meso‐diastereomer, exhibit significantly enhanced molar optical rotations due to the presence of three helically arranged 1,2‐dicyclopropylethane units in their skeletons.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200801111</doi><tpages>5</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Chirality Density functional calculations Exact sciences and technology Helical structures Oligocyclic cyclopropane derivatives Organic chemistry Preparations and properties Small ring systems |
| title | 1,1′-Bi(trishomobarrelenyl) - Synthesis and Chiroptic Properties |
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