Catalytic Asymmetric Synthesis of Silicon‐Stereogenic Dihydrodibenzosilines: Silicon Central‐to‐Axial Chirality Relay
A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. In the presence of a RhI catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon‐central and axial ch...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie 2021-06, Vol.133 (25), p.14006-14010 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 14010 |
|---|---|
| container_issue | 25 |
| container_start_page | 14006 |
| container_title | Angewandte Chemie |
| container_volume | 133 |
| creator | Guo, Yonghong Liu, Meng‐Meng Zhu, Xujiang Zhu, Liru He, Chuan |
| description | A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. In the presence of a RhI catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon‐central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative C(sp3)−H silylation. Absolute configuration analysis by single‐crystal X‐ray structures revealed a novel silicon central‐to‐axial chirality relay phenomenon, which we believe will inspire further research in the field of asymmetric catalysis and chiroptical materials.
A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. A wide range of dihydrodibenzosilines containing both silicon‐central and axial chirality are conveniently constructed in excellent enantioselectivity via intramolecular dehydrogenative C−H silylation. |
| doi_str_mv | 10.1002/ange.202103748 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2537431410</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2537431410</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2288-6adf6d95eceb713d3ca492d81bab8e0a8b8bdab5518940778a885d2cf6c591863</originalsourceid><addsrcrecordid>eNqFkL9OwzAQhy0EEqWwMkdiTrGdOHHYolAKUgUShTlynEvrKo2L7QoCC4_AM_IkuCp_Rpa70-n73UkfQqcEjwjG9Fx0cxhRTAmO0pjvoQFhlIRRytJ9NMA4jkNO4-wQHVm7xBgnNM0G6K0QTrS9UzLIbb9agTN-nPWdW4BVNtBNMFOtkrr7fP-YOTCg59B55FIt-troWlXQvWrrmQ7sxQ8cFNA5I1ofctqX_EWJNigWyu-U64N7aEV_jA4a0Vo4-e5D9Hg1fiiuw-nd5KbIp6GklPMwEXWT1BkDCVVKojqSIs5ozUklKg5Y8IpXtagYIzyLcZpywTmrqWwSyTLCk2iIznZ310Y_bcC6cqk3pvMvS8q8q4jE3tkQjXaUNNpaA025NmolTF8SXG4Fl1vB5a9gH8h2gWfVQv8PXea3k_Ff9guknYU7</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2537431410</pqid></control><display><type>article</type><title>Catalytic Asymmetric Synthesis of Silicon‐Stereogenic Dihydrodibenzosilines: Silicon Central‐to‐Axial Chirality Relay</title><source>Wiley Online Library All Journals</source><creator>Guo, Yonghong ; Liu, Meng‐Meng ; Zhu, Xujiang ; Zhu, Liru ; He, Chuan</creator><creatorcontrib>Guo, Yonghong ; Liu, Meng‐Meng ; Zhu, Xujiang ; Zhu, Liru ; He, Chuan</creatorcontrib><description>A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. In the presence of a RhI catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon‐central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative C(sp3)−H silylation. Absolute configuration analysis by single‐crystal X‐ray structures revealed a novel silicon central‐to‐axial chirality relay phenomenon, which we believe will inspire further research in the field of asymmetric catalysis and chiroptical materials.
A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. A wide range of dihydrodibenzosilines containing both silicon‐central and axial chirality are conveniently constructed in excellent enantioselectivity via intramolecular dehydrogenative C−H silylation.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202103748</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Absolute configuration ; Asymmetric synthesis ; Asymmetry ; axial chirality ; Catalysis ; Catalysts ; Chemical synthesis ; Chemistry ; Chirality ; chirality relay ; Crystal structure ; Dehydrogenation ; enantioselective C−H silylation ; Relay ; Silicon ; silicon-central chirality ; silicon-stereogenic monohydrosilanes</subject><ispartof>Angewandte Chemie, 2021-06, Vol.133 (25), p.14006-14010</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2288-6adf6d95eceb713d3ca492d81bab8e0a8b8bdab5518940778a885d2cf6c591863</citedby><cites>FETCH-LOGICAL-c2288-6adf6d95eceb713d3ca492d81bab8e0a8b8bdab5518940778a885d2cf6c591863</cites><orcidid>0000-0002-9983-7526</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%2Fange.202103748$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.202103748$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Guo, Yonghong</creatorcontrib><creatorcontrib>Liu, Meng‐Meng</creatorcontrib><creatorcontrib>Zhu, Xujiang</creatorcontrib><creatorcontrib>Zhu, Liru</creatorcontrib><creatorcontrib>He, Chuan</creatorcontrib><title>Catalytic Asymmetric Synthesis of Silicon‐Stereogenic Dihydrodibenzosilines: Silicon Central‐to‐Axial Chirality Relay</title><title>Angewandte Chemie</title><description>A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. In the presence of a RhI catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon‐central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative C(sp3)−H silylation. Absolute configuration analysis by single‐crystal X‐ray structures revealed a novel silicon central‐to‐axial chirality relay phenomenon, which we believe will inspire further research in the field of asymmetric catalysis and chiroptical materials.
A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. A wide range of dihydrodibenzosilines containing both silicon‐central and axial chirality are conveniently constructed in excellent enantioselectivity via intramolecular dehydrogenative C−H silylation.</description><subject>Absolute configuration</subject><subject>Asymmetric synthesis</subject><subject>Asymmetry</subject><subject>axial chirality</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chirality</subject><subject>chirality relay</subject><subject>Crystal structure</subject><subject>Dehydrogenation</subject><subject>enantioselective C−H silylation</subject><subject>Relay</subject><subject>Silicon</subject><subject>silicon-central chirality</subject><subject>silicon-stereogenic monohydrosilanes</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkL9OwzAQhy0EEqWwMkdiTrGdOHHYolAKUgUShTlynEvrKo2L7QoCC4_AM_IkuCp_Rpa70-n73UkfQqcEjwjG9Fx0cxhRTAmO0pjvoQFhlIRRytJ9NMA4jkNO4-wQHVm7xBgnNM0G6K0QTrS9UzLIbb9agTN-nPWdW4BVNtBNMFOtkrr7fP-YOTCg59B55FIt-troWlXQvWrrmQ7sxQ8cFNA5I1ofctqX_EWJNigWyu-U64N7aEV_jA4a0Vo4-e5D9Hg1fiiuw-nd5KbIp6GklPMwEXWT1BkDCVVKojqSIs5ozUklKg5Y8IpXtagYIzyLcZpywTmrqWwSyTLCk2iIznZ310Y_bcC6cqk3pvMvS8q8q4jE3tkQjXaUNNpaA025NmolTF8SXG4Fl1vB5a9gH8h2gWfVQv8PXea3k_Ff9guknYU7</recordid><startdate>20210614</startdate><enddate>20210614</enddate><creator>Guo, Yonghong</creator><creator>Liu, Meng‐Meng</creator><creator>Zhu, Xujiang</creator><creator>Zhu, Liru</creator><creator>He, Chuan</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-9983-7526</orcidid></search><sort><creationdate>20210614</creationdate><title>Catalytic Asymmetric Synthesis of Silicon‐Stereogenic Dihydrodibenzosilines: Silicon Central‐to‐Axial Chirality Relay</title><author>Guo, Yonghong ; Liu, Meng‐Meng ; Zhu, Xujiang ; Zhu, Liru ; He, Chuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2288-6adf6d95eceb713d3ca492d81bab8e0a8b8bdab5518940778a885d2cf6c591863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Absolute configuration</topic><topic>Asymmetric synthesis</topic><topic>Asymmetry</topic><topic>axial chirality</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chirality</topic><topic>chirality relay</topic><topic>Crystal structure</topic><topic>Dehydrogenation</topic><topic>enantioselective C−H silylation</topic><topic>Relay</topic><topic>Silicon</topic><topic>silicon-central chirality</topic><topic>silicon-stereogenic monohydrosilanes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Yonghong</creatorcontrib><creatorcontrib>Liu, Meng‐Meng</creatorcontrib><creatorcontrib>Zhu, Xujiang</creatorcontrib><creatorcontrib>Zhu, Liru</creatorcontrib><creatorcontrib>He, Chuan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guo, Yonghong</au><au>Liu, Meng‐Meng</au><au>Zhu, Xujiang</au><au>Zhu, Liru</au><au>He, Chuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Asymmetric Synthesis of Silicon‐Stereogenic Dihydrodibenzosilines: Silicon Central‐to‐Axial Chirality Relay</atitle><jtitle>Angewandte Chemie</jtitle><date>2021-06-14</date><risdate>2021</risdate><volume>133</volume><issue>25</issue><spage>14006</spage><epage>14010</epage><pages>14006-14010</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. In the presence of a RhI catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon‐central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative C(sp3)−H silylation. Absolute configuration analysis by single‐crystal X‐ray structures revealed a novel silicon central‐to‐axial chirality relay phenomenon, which we believe will inspire further research in the field of asymmetric catalysis and chiroptical materials.
A Rh‐catalyzed asymmetric synthesis of silicon‐stereogenic dihydrodibenzosilines featuring axially chiral 6‐membered bridged biaryls is demonstrated. A wide range of dihydrodibenzosilines containing both silicon‐central and axial chirality are conveniently constructed in excellent enantioselectivity via intramolecular dehydrogenative C−H silylation.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.202103748</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9983-7526</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0044-8249 |
| ispartof | Angewandte Chemie, 2021-06, Vol.133 (25), p.14006-14010 |
| issn | 0044-8249 1521-3757 |
| language | eng |
| recordid | cdi_proquest_journals_2537431410 |
| source | Wiley Online Library All Journals |
| subjects | Absolute configuration Asymmetric synthesis Asymmetry axial chirality Catalysis Catalysts Chemical synthesis Chemistry Chirality chirality relay Crystal structure Dehydrogenation enantioselective C−H silylation Relay Silicon silicon-central chirality silicon-stereogenic monohydrosilanes |
| title | Catalytic Asymmetric Synthesis of Silicon‐Stereogenic Dihydrodibenzosilines: Silicon Central‐to‐Axial Chirality Relay |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T12%3A13%3A39IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Catalytic%20Asymmetric%20Synthesis%20of%20Silicon%E2%80%90Stereogenic%20Dihydrodibenzosilines:%20Silicon%20Central%E2%80%90to%E2%80%90Axial%20Chirality%20Relay&rft.jtitle=Angewandte%20Chemie&rft.au=Guo,%20Yonghong&rft.date=2021-06-14&rft.volume=133&rft.issue=25&rft.spage=14006&rft.epage=14010&rft.pages=14006-14010&rft.issn=0044-8249&rft.eissn=1521-3757&rft_id=info:doi/10.1002/ange.202103748&rft_dat=%3Cproquest_cross%3E2537431410%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2537431410&rft_id=info:pmid/&rfr_iscdi=true |