Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular syn...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2020-12, Vol.59 (52), p.23527-23531 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 23531 |
|---|---|
| container_issue | 52 |
| container_start_page | 23527 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 59 |
| creator | Redero, Pablo Hartung, Thierry Zhang, Jianwei Nicholls, Leo D. M. Zichen, Guo Simon, Martin Golz, Christopher Alcarazo, Manuel |
| description | The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to AuI‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
A new family of α‐cationic phosphonites derived from BINOL has been synthesized. Their use as ancillary ligands in AuI catalysis allows the enantioselective assembly of 1‐aryl [5]helicenes with excellent yields and in up to 98 % ee. |
| doi_str_mv | 10.1002/anie.202010021 |
| format | Article |
| fullrecord | <record><control><sourceid>wiley_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7756570</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ANIE202010021</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5101-ade55d26f6708edbe0db015930bcabff0adc44e173b069fa4025a89d81d1dc153</originalsourceid><addsrcrecordid>eNqFkc9OAjEQhxujEUSvHk1fYLHdpfvnYgKISkLARDkZ03TbWbZm6ZLtillPPoLP6JNYgqKePHWafr-vkxmETinpUkL8c2E0dH3ik82N7qE2ZT71gigK9l3dCwIvihltoSNrnxwRxyQ8RK3Aj5MwSZI2akZGmFqXFgqQtV4DvmtMnYPVFpcZph9v7_2qKfAAzGv5wB5zKLQEAxbPrTYLPBhPZxMHXULlwgoPhZMZLfFtXtpV7srascLivpG6KETV4IleCKPsMTrIRGHh5OvsoPnV6H54401m1-Nhf-JJRgn1hALGlB9mYURiUCkQlRLKkoCkUqRZRoSSvR7QKEhJmGSiR3wm4kTFVFElKQs66GLrXT2nS1Cu-boSBV9Veum64aXQ_O-L0TlflGseRSxkEXGC7lYgq9LaCrJdlhK-GTvfLIHvluACZ79_3OHfU3dAsgVedAHNPzren45HP_JPhpuZVw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands</title><source>Access via Wiley Online Library</source><creator>Redero, Pablo ; Hartung, Thierry ; Zhang, Jianwei ; Nicholls, Leo D. M. ; Zichen, Guo ; Simon, Martin ; Golz, Christopher ; Alcarazo, Manuel</creator><creatorcontrib>Redero, Pablo ; Hartung, Thierry ; Zhang, Jianwei ; Nicholls, Leo D. M. ; Zichen, Guo ; Simon, Martin ; Golz, Christopher ; Alcarazo, Manuel</creatorcontrib><description>The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to AuI‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
A new family of α‐cationic phosphonites derived from BINOL has been synthesized. Their use as ancillary ligands in AuI catalysis allows the enantioselective assembly of 1‐aryl [5]helicenes with excellent yields and in up to 98 % ee.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202010021</identifier><identifier>PMID: 32896999</identifier><language>eng</language><publisher>Germany: John Wiley and Sons Inc</publisher><subject>asymmetric catalysis ; cationic phosphonites ; Communication ; Communications ; gold catalysis ; helicenes ; ligand design</subject><ispartof>Angewandte Chemie International Edition, 2020-12, Vol.59 (52), p.23527-23531</ispartof><rights>2020 The Authors. Published by Wiley-VCH GmbH</rights><rights>2020 The Authors. Published by Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5101-ade55d26f6708edbe0db015930bcabff0adc44e173b069fa4025a89d81d1dc153</citedby><cites>FETCH-LOGICAL-c5101-ade55d26f6708edbe0db015930bcabff0adc44e173b069fa4025a89d81d1dc153</cites><orcidid>0000-0002-5491-5682</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%2Fanie.202010021$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202010021$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,781,785,886,1418,27926,27927,45576,45577</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32896999$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Redero, Pablo</creatorcontrib><creatorcontrib>Hartung, Thierry</creatorcontrib><creatorcontrib>Zhang, Jianwei</creatorcontrib><creatorcontrib>Nicholls, Leo D. M.</creatorcontrib><creatorcontrib>Zichen, Guo</creatorcontrib><creatorcontrib>Simon, Martin</creatorcontrib><creatorcontrib>Golz, Christopher</creatorcontrib><creatorcontrib>Alcarazo, Manuel</creatorcontrib><title>Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to AuI‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
A new family of α‐cationic phosphonites derived from BINOL has been synthesized. Their use as ancillary ligands in AuI catalysis allows the enantioselective assembly of 1‐aryl [5]helicenes with excellent yields and in up to 98 % ee.</description><subject>asymmetric catalysis</subject><subject>cationic phosphonites</subject><subject>Communication</subject><subject>Communications</subject><subject>gold catalysis</subject><subject>helicenes</subject><subject>ligand design</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkc9OAjEQhxujEUSvHk1fYLHdpfvnYgKISkLARDkZ03TbWbZm6ZLtillPPoLP6JNYgqKePHWafr-vkxmETinpUkL8c2E0dH3ik82N7qE2ZT71gigK9l3dCwIvihltoSNrnxwRxyQ8RK3Aj5MwSZI2akZGmFqXFgqQtV4DvmtMnYPVFpcZph9v7_2qKfAAzGv5wB5zKLQEAxbPrTYLPBhPZxMHXULlwgoPhZMZLfFtXtpV7srascLivpG6KETV4IleCKPsMTrIRGHh5OvsoPnV6H54401m1-Nhf-JJRgn1hALGlB9mYURiUCkQlRLKkoCkUqRZRoSSvR7QKEhJmGSiR3wm4kTFVFElKQs66GLrXT2nS1Cu-boSBV9Veum64aXQ_O-L0TlflGseRSxkEXGC7lYgq9LaCrJdlhK-GTvfLIHvluACZ79_3OHfU3dAsgVedAHNPzren45HP_JPhpuZVw</recordid><startdate>20201221</startdate><enddate>20201221</enddate><creator>Redero, Pablo</creator><creator>Hartung, Thierry</creator><creator>Zhang, Jianwei</creator><creator>Nicholls, Leo D. M.</creator><creator>Zichen, Guo</creator><creator>Simon, Martin</creator><creator>Golz, Christopher</creator><creator>Alcarazo, Manuel</creator><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-5491-5682</orcidid></search><sort><creationdate>20201221</creationdate><title>Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands</title><author>Redero, Pablo ; Hartung, Thierry ; Zhang, Jianwei ; Nicholls, Leo D. M. ; Zichen, Guo ; Simon, Martin ; Golz, Christopher ; Alcarazo, Manuel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5101-ade55d26f6708edbe0db015930bcabff0adc44e173b069fa4025a89d81d1dc153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>asymmetric catalysis</topic><topic>cationic phosphonites</topic><topic>Communication</topic><topic>Communications</topic><topic>gold catalysis</topic><topic>helicenes</topic><topic>ligand design</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Redero, Pablo</creatorcontrib><creatorcontrib>Hartung, Thierry</creatorcontrib><creatorcontrib>Zhang, Jianwei</creatorcontrib><creatorcontrib>Nicholls, Leo D. M.</creatorcontrib><creatorcontrib>Zichen, Guo</creatorcontrib><creatorcontrib>Simon, Martin</creatorcontrib><creatorcontrib>Golz, Christopher</creatorcontrib><creatorcontrib>Alcarazo, Manuel</creatorcontrib><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library (Open Access Collection)</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Redero, Pablo</au><au>Hartung, Thierry</au><au>Zhang, Jianwei</au><au>Nicholls, Leo D. M.</au><au>Zichen, Guo</au><au>Simon, Martin</au><au>Golz, Christopher</au><au>Alcarazo, Manuel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-12-21</date><risdate>2020</risdate><volume>59</volume><issue>52</issue><spage>23527</spage><epage>23531</epage><pages>23527-23531</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to AuI‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
A new family of α‐cationic phosphonites derived from BINOL has been synthesized. Their use as ancillary ligands in AuI catalysis allows the enantioselective assembly of 1‐aryl [5]helicenes with excellent yields and in up to 98 % ee.</abstract><cop>Germany</cop><pub>John Wiley and Sons Inc</pub><pmid>32896999</pmid><doi>10.1002/anie.202010021</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5491-5682</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2020-12, Vol.59 (52), p.23527-23531 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7756570 |
| source | Access via Wiley Online Library |
| subjects | asymmetric catalysis cationic phosphonites Communication Communications gold catalysis helicenes ligand design |
| title | Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T09%3A13%3A32IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Enantioselective%20Synthesis%20of%201%E2%80%90Aryl%20Benzo%5B5%5Dhelicenes%20Using%20BINOL%E2%80%90Derived%20Cationic%20Phosphonites%20as%20Ancillary%20Ligands&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Redero,%20Pablo&rft.date=2020-12-21&rft.volume=59&rft.issue=52&rft.spage=23527&rft.epage=23531&rft.pages=23527-23531&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.202010021&rft_dat=%3Cwiley_pubme%3EANIE202010021%3C/wiley_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/32896999&rfr_iscdi=true |