A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration
3,14-Dihydroxy[6]helicene 4 was prepared, in a good yield, through a “4 + 1” approach involving the Mizoroki–Heck coupling reaction followed by oxidative photodehydrocylisation. Resolution of this racemic helicenediol was performed by HPLC on a chiral stationary phase, providing both enantiomers (−)...
Gespeichert in:
| Veröffentlicht in: | Comptes rendus. Chimie 2009-01, Vol.12 (1), p.284-290 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 290 |
|---|---|
| container_issue | 1 |
| container_start_page | 284 |
| container_title | Comptes rendus. Chimie |
| container_volume | 12 |
| creator | Aloui, Faouzi El Abed, Riadh Marinetti, Angéla Ben Hassine, Béchir |
| description | 3,14-Dihydroxy[6]helicene
4 was prepared, in a good yield, through a “4
+
1” approach involving the Mizoroki–Heck coupling reaction followed by oxidative photodehydrocylisation. Resolution of this racemic helicenediol was performed by HPLC on a chiral stationary phase, providing both enantiomers (−)- and (+)-
4 with high optical purity. The absolute configurations of (−)- and (+)-
4 were assigned as
M and
P, respectively, by means of circular dichroism spectroscopy.
Le 3,14-dihydroxy[6]hélicène
4 a été préparé, avec un bon rendement chimique, via une approche «
4
+
1
» impliquant la réaction de couplage de Mizoroki–Heck suivie d'une photocyclodéhydrogénation oxydante. Le dédoublement de ce diol hélicénique a été accompli par HPLC sur phase chirale stationnaire conduisant aux deux énantiomères (−)- et (+)-
4 avec une haute pureté optique. Les configurations absolues
M et
P ont été attribuées à (−)- et (+)-
4, respectivement, au moyen de la spectroscopie du dichroïsme circulaire. |
| doi_str_mv | 10.1016/j.crci.2008.01.009 |
| format | Article |
| fullrecord | <record><control><sourceid>hal_cross</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00433260v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S1631074808000192</els_id><sourcerecordid>oai_HAL_hal_00433260v1</sourcerecordid><originalsourceid>FETCH-LOGICAL-c430t-d8880a616df3a9731e1ef155c0350352d40a7be1f0d9c128eaa38026940786983</originalsourceid><addsrcrecordid>eNp9kE2LFDEQhhtRcF39A55y8SDYbVWnPxLxMiy6KwwIoudQk1TsDG1nSHo_5t_bbS97FAKVVJ6nQt6ieItQIWD38VjZZENVA6gKsALQz4oLVL0qsW3k82XfSSyhb9TL4lXOR1gk3XYXhd-Jie8FnU4pkh3EHIX8gE3pwnB2KT6cB36ggcdgeeJP4gfnON7OIU6CJidonlM4bOfoxTywoMM_goWNkw-_bxOtt6-LF57GzG8e62Xx6-uXn1c35f779ber3b60jYS5dEopoA475yXpXiIje2xbC7JdVu0aoP7A6MFpi7ViIqmg7nQDveq0kpfF-23uQKM5pfCH0tlECuZmtzdrD6CRsu7gDhe23libYs6J_ZOAYNZUzdGsqZo1VQO4uHqR3m3SibKl0SeabMhPZo2t0lo1C_d543j57V3gZLINPFl2IbGdjYvhf8_8BTXDjO0</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration</title><source>Elsevier ScienceDirect Journals Complete</source><source>Free E-Journal (出版社公開部分のみ）</source><creator>Aloui, Faouzi ; El Abed, Riadh ; Marinetti, Angéla ; Ben Hassine, Béchir</creator><creatorcontrib>Aloui, Faouzi ; El Abed, Riadh ; Marinetti, Angéla ; Ben Hassine, Béchir</creatorcontrib><description>3,14-Dihydroxy[6]helicene
4 was prepared, in a good yield, through a “4
+
1” approach involving the Mizoroki–Heck coupling reaction followed by oxidative photodehydrocylisation. Resolution of this racemic helicenediol was performed by HPLC on a chiral stationary phase, providing both enantiomers (−)- and (+)-
4 with high optical purity. The absolute configurations of (−)- and (+)-
4 were assigned as
M and
P, respectively, by means of circular dichroism spectroscopy.
Le 3,14-dihydroxy[6]hélicène
4 a été préparé, avec un bon rendement chimique, via une approche «
4
+
1
» impliquant la réaction de couplage de Mizoroki–Heck suivie d'une photocyclodéhydrogénation oxydante. Le dédoublement de ce diol hélicénique a été accompli par HPLC sur phase chirale stationnaire conduisant aux deux énantiomères (−)- et (+)-
4 avec une haute pureté optique. Les configurations absolues
M et
P ont été attribuées à (−)- et (+)-
4, respectivement, au moyen de la spectroscopie du dichroïsme circulaire.</description><identifier>ISSN: 1631-0748</identifier><identifier>ISSN: 1878-1543</identifier><identifier>EISSN: 1878-1543</identifier><identifier>DOI: 10.1016/j.crci.2008.01.009</identifier><language>eng</language><publisher>Paris: Elsevier SAS</publisher><subject>Alcools hélicoïdaux ; Chemical Sciences ; Chemistry ; Dédoublement ; Enantiomeric resolution ; Exact sciences and technology ; General and physical chemistry ; Heck reaction ; Helical alcohols ; Helicenes ; Hélicènes ; Organic chemistry ; Photochemistry ; Photodehydrocyclisation ; Photodéhydrocyclisation ; Physical chemistry of induced reactions (with radiations, particles and ultrasonics) ; Réaction de Heck</subject><ispartof>Comptes rendus. Chimie, 2009-01, Vol.12 (1), p.284-290</ispartof><rights>2008 Académie des sciences</rights><rights>2009 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c430t-d8880a616df3a9731e1ef155c0350352d40a7be1f0d9c128eaa38026940786983</citedby><cites>FETCH-LOGICAL-c430t-d8880a616df3a9731e1ef155c0350352d40a7be1f0d9c128eaa38026940786983</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.crci.2008.01.009$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21589984$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00433260$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Aloui, Faouzi</creatorcontrib><creatorcontrib>El Abed, Riadh</creatorcontrib><creatorcontrib>Marinetti, Angéla</creatorcontrib><creatorcontrib>Ben Hassine, Béchir</creatorcontrib><title>A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration</title><title>Comptes rendus. Chimie</title><description>3,14-Dihydroxy[6]helicene
4 was prepared, in a good yield, through a “4
+
1” approach involving the Mizoroki–Heck coupling reaction followed by oxidative photodehydrocylisation. Resolution of this racemic helicenediol was performed by HPLC on a chiral stationary phase, providing both enantiomers (−)- and (+)-
4 with high optical purity. The absolute configurations of (−)- and (+)-
4 were assigned as
M and
P, respectively, by means of circular dichroism spectroscopy.
Le 3,14-dihydroxy[6]hélicène
4 a été préparé, avec un bon rendement chimique, via une approche «
4
+
1
» impliquant la réaction de couplage de Mizoroki–Heck suivie d'une photocyclodéhydrogénation oxydante. Le dédoublement de ce diol hélicénique a été accompli par HPLC sur phase chirale stationnaire conduisant aux deux énantiomères (−)- et (+)-
4 avec une haute pureté optique. Les configurations absolues
M et
P ont été attribuées à (−)- et (+)-
4, respectivement, au moyen de la spectroscopie du dichroïsme circulaire.</description><subject>Alcools hélicoïdaux</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Dédoublement</subject><subject>Enantiomeric resolution</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heck reaction</subject><subject>Helical alcohols</subject><subject>Helicenes</subject><subject>Hélicènes</subject><subject>Organic chemistry</subject><subject>Photochemistry</subject><subject>Photodehydrocyclisation</subject><subject>Photodéhydrocyclisation</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>Réaction de Heck</subject><issn>1631-0748</issn><issn>1878-1543</issn><issn>1878-1543</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp9kE2LFDEQhhtRcF39A55y8SDYbVWnPxLxMiy6KwwIoudQk1TsDG1nSHo_5t_bbS97FAKVVJ6nQt6ieItQIWD38VjZZENVA6gKsALQz4oLVL0qsW3k82XfSSyhb9TL4lXOR1gk3XYXhd-Jie8FnU4pkh3EHIX8gE3pwnB2KT6cB36ggcdgeeJP4gfnON7OIU6CJidonlM4bOfoxTywoMM_goWNkw-_bxOtt6-LF57GzG8e62Xx6-uXn1c35f779ber3b60jYS5dEopoA475yXpXiIje2xbC7JdVu0aoP7A6MFpi7ViIqmg7nQDveq0kpfF-23uQKM5pfCH0tlECuZmtzdrD6CRsu7gDhe23libYs6J_ZOAYNZUzdGsqZo1VQO4uHqR3m3SibKl0SeabMhPZo2t0lo1C_d543j57V3gZLINPFl2IbGdjYvhf8_8BTXDjO0</recordid><startdate>20090101</startdate><enddate>20090101</enddate><creator>Aloui, Faouzi</creator><creator>El Abed, Riadh</creator><creator>Marinetti, Angéla</creator><creator>Ben Hassine, Béchir</creator><general>Elsevier SAS</general><general>Elsevier</general><general>Académie des sciences (Paris)</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope></search><sort><creationdate>20090101</creationdate><title>A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration</title><author>Aloui, Faouzi ; El Abed, Riadh ; Marinetti, Angéla ; Ben Hassine, Béchir</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c430t-d8880a616df3a9731e1ef155c0350352d40a7be1f0d9c128eaa38026940786983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alcools hélicoïdaux</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Dédoublement</topic><topic>Enantiomeric resolution</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heck reaction</topic><topic>Helical alcohols</topic><topic>Helicenes</topic><topic>Hélicènes</topic><topic>Organic chemistry</topic><topic>Photochemistry</topic><topic>Photodehydrocyclisation</topic><topic>Photodéhydrocyclisation</topic><topic>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</topic><topic>Réaction de Heck</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aloui, Faouzi</creatorcontrib><creatorcontrib>El Abed, Riadh</creatorcontrib><creatorcontrib>Marinetti, Angéla</creatorcontrib><creatorcontrib>Ben Hassine, Béchir</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Comptes rendus. Chimie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aloui, Faouzi</au><au>El Abed, Riadh</au><au>Marinetti, Angéla</au><au>Ben Hassine, Béchir</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration</atitle><jtitle>Comptes rendus. Chimie</jtitle><date>2009-01-01</date><risdate>2009</risdate><volume>12</volume><issue>1</issue><spage>284</spage><epage>290</epage><pages>284-290</pages><issn>1631-0748</issn><issn>1878-1543</issn><eissn>1878-1543</eissn><abstract>3,14-Dihydroxy[6]helicene
4 was prepared, in a good yield, through a “4
+
1” approach involving the Mizoroki–Heck coupling reaction followed by oxidative photodehydrocylisation. Resolution of this racemic helicenediol was performed by HPLC on a chiral stationary phase, providing both enantiomers (−)- and (+)-
4 with high optical purity. The absolute configurations of (−)- and (+)-
4 were assigned as
M and
P, respectively, by means of circular dichroism spectroscopy.
Le 3,14-dihydroxy[6]hélicène
4 a été préparé, avec un bon rendement chimique, via une approche «
4
+
1
» impliquant la réaction de couplage de Mizoroki–Heck suivie d'une photocyclodéhydrogénation oxydante. Le dédoublement de ce diol hélicénique a été accompli par HPLC sur phase chirale stationnaire conduisant aux deux énantiomères (−)- et (+)-
4 avec une haute pureté optique. Les configurations absolues
M et
P ont été attribuées à (−)- et (+)-
4, respectivement, au moyen de la spectroscopie du dichroïsme circulaire.</abstract><cop>Paris</cop><pub>Elsevier SAS</pub><doi>10.1016/j.crci.2008.01.009</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1631-0748 |
| ispartof | Comptes rendus. Chimie, 2009-01, Vol.12 (1), p.284-290 |
| issn | 1631-0748 1878-1543 1878-1543 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00433260v1 |
| source | Elsevier ScienceDirect Journals Complete; Free E-Journal (出版社公開部分のみ） |
| subjects | Alcools hélicoïdaux Chemical Sciences Chemistry Dédoublement Enantiomeric resolution Exact sciences and technology General and physical chemistry Heck reaction Helical alcohols Helicenes Hélicènes Organic chemistry Photochemistry Photodehydrocyclisation Photodéhydrocyclisation Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Réaction de Heck |
| title | A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T09%3A10%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-hal_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20new%20approach%20to%203,14-dihydroxyhexahelicene:%20Resolution%20and%20attribution%20of%20the%20absolute%20configuration&rft.jtitle=Comptes%20rendus.%20Chimie&rft.au=Aloui,%20Faouzi&rft.date=2009-01-01&rft.volume=12&rft.issue=1&rft.spage=284&rft.epage=290&rft.pages=284-290&rft.issn=1631-0748&rft.eissn=1878-1543&rft_id=info:doi/10.1016/j.crci.2008.01.009&rft_dat=%3Chal_cross%3Eoai_HAL_hal_00433260v1%3C/hal_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rft_els_id=S1631074808000192&rfr_iscdi=true |