Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides
A formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides via visible light-driven photoredox catalysis is reported. Under transition metal-free conditions using a dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst, the transformation was efficient and led to...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2019-09, Vol.55 (77), p.11527-11530 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Liu, Xiangyuan Yin, Yanli Jiang, Zhiyong |
| description | A formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides via visible light-driven photoredox catalysis is reported. Under transition metal-free conditions using a dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst, the transformation was efficient and led to a series of important diazabicyclo[3.2.1]octane-based N-heterocyclic compounds. This work demonstrates the synthetic utility of N-aryl α-amino acids as 1,2-synthons and provides a new strategy for the dearomatization of isoquinolines. |
| doi_str_mv | 10.1039/c9cc06249a |
| format | Article |
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Under transition metal-free conditions using a dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst, the transformation was efficient and led to a series of important diazabicyclo[3.2.1]octane-based N-heterocyclic compounds. 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This work demonstrates the synthetic utility of N-aryl α-amino acids as 1,2-synthons and provides a new strategy for the dearomatization of isoquinolines.</description><subject>Amino acids</subject><subject>Aromatic compounds</subject><subject>Chromophores</subject><subject>Crystallography</subject><subject>Cycloaddition</subject><subject>Heterocyclic compounds</subject><subject>Photoredox catalysis</subject><subject>Transition metals</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkN2KFDEQhcOi7Kzj3uwDSMCbRWnNT6W7czk0uyosuhcKgkiTqSRMhu7O2OnGmcfyRfaZzDqjF9ZNFcXH4ZxDyBVnbziT-i1qRFYK0OaMXHBZQqGg_vrk8Va6qCSoBXmW0pbl4ao-JwvJQTOo6wuC95s4xdHZuC_QTKY7JGepj2NvOvpNvhbfKR6wi8baMIU40Ojpx8KMh44-_CpMH4ZIDQab6M8wbWhI8cecf10YXObiPliXnpOn3nTJXZ72kny5vfncvC_uPr370KzuCpRcTQUyA9agZEaAgjVnJfcK0HGoAXJG63kFtUdnq8p5hw4VE1poVQoB6Gu5JNdH3d2YXbg0tX1I6LrODC7OqRWiLrUEzlhGX_6HbuM8DtldpnSppIYKMvXqSOEYUxqdb3dj6HP4lrP2sfq20U3zp_pVhl-cJOd17-w_9G_X8jdyxH7-</recordid><startdate>20190924</startdate><enddate>20190924</enddate><creator>Liu, Xiangyuan</creator><creator>Yin, Yanli</creator><creator>Jiang, Zhiyong</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6350-7429</orcidid></search><sort><creationdate>20190924</creationdate><title>Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides</title><author>Liu, Xiangyuan ; Yin, Yanli ; Jiang, Zhiyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-c0a4dac30a2454b1061f54ce14844c9cdf1748fced77efecec50292956224cf83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Amino acids</topic><topic>Aromatic compounds</topic><topic>Chromophores</topic><topic>Crystallography</topic><topic>Cycloaddition</topic><topic>Heterocyclic compounds</topic><topic>Photoredox catalysis</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Xiangyuan</creatorcontrib><creatorcontrib>Yin, Yanli</creatorcontrib><creatorcontrib>Jiang, Zhiyong</creatorcontrib><collection>PubMed</collection><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><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Xiangyuan</au><au>Yin, Yanli</au><au>Jiang, Zhiyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2019-09-24</date><risdate>2019</risdate><volume>55</volume><issue>77</issue><spage>11527</spage><epage>11530</epage><pages>11527-11530</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides via visible light-driven photoredox catalysis is reported. 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| ispartof | Chemical communications (Cambridge, England), 2019-09, Vol.55 (77), p.11527-11530 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amino acids Aromatic compounds Chromophores Crystallography Cycloaddition Heterocyclic compounds Photoredox catalysis Transition metals |
| title | Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides |
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