Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible‐Light Photocatalysis
Herein we report the first redox‐neutral visible‐light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible‐light‐promoted cycloadditions with conjugated carbo...
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| Veröffentlicht in: | ChemPhotoChem 2023-03, Vol.7 (3), p.n/a |
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| creator | Trieu, Phillip Filkin, William H. Pinarci, Ali Tobias, Elisa M. Madiu, Rufai Dellosso, Brandon Roldan, Justin Das, Pulakesh Austin, Brooke E. Moura‐Letts, Gustavo |
| description | Herein we report the first redox‐neutral visible‐light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible‐light‐promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox‐neutral pathway is proposed as the primary photoredox mechanism for this transformation.
Redox neutral pathway: This effort highlights the first highly stereoselective photocatalytic dipolar cycloaddition of vinyl nitrones and conjugated carbonyl derivatives. This method allows for the synthesis of complex heterocycles under very mild conditions with good yields and selectivities. The data observed justifies a potential redox‐neutral photocatalytic pathway for the observed products. |
| doi_str_mv | 10.1002/cptc.202200277 |
| format | Article |
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Redox neutral pathway: This effort highlights the first highly stereoselective photocatalytic dipolar cycloaddition of vinyl nitrones and conjugated carbonyl derivatives. This method allows for the synthesis of complex heterocycles under very mild conditions with good yields and selectivities. The data observed justifies a potential redox‐neutral photocatalytic pathway for the observed products.</description><identifier>ISSN: 2367-0932</identifier><identifier>EISSN: 2367-0932</identifier><identifier>DOI: 10.1002/cptc.202200277</identifier><language>eng</language><subject>dipolar cycloadditions ; heterocycles ; isoxazolidines ; photocatalysis ; vinyl nitrones</subject><ispartof>ChemPhotoChem, 2023-03, Vol.7 (3), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2897-e21997868a54760613b781ac87798b423ffd4c06e3df4fb64f61d6afea5c8d3f3</citedby><cites>FETCH-LOGICAL-c2897-e21997868a54760613b781ac87798b423ffd4c06e3df4fb64f61d6afea5c8d3f3</cites><orcidid>0000-0001-8156-151X</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%2Fcptc.202200277$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcptc.202200277$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Trieu, Phillip</creatorcontrib><creatorcontrib>Filkin, William H.</creatorcontrib><creatorcontrib>Pinarci, Ali</creatorcontrib><creatorcontrib>Tobias, Elisa M.</creatorcontrib><creatorcontrib>Madiu, Rufai</creatorcontrib><creatorcontrib>Dellosso, Brandon</creatorcontrib><creatorcontrib>Roldan, Justin</creatorcontrib><creatorcontrib>Das, Pulakesh</creatorcontrib><creatorcontrib>Austin, Brooke E.</creatorcontrib><creatorcontrib>Moura‐Letts, Gustavo</creatorcontrib><title>Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible‐Light Photocatalysis</title><title>ChemPhotoChem</title><description>Herein we report the first redox‐neutral visible‐light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible‐light‐promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox‐neutral pathway is proposed as the primary photoredox mechanism for this transformation.
Redox neutral pathway: This effort highlights the first highly stereoselective photocatalytic dipolar cycloaddition of vinyl nitrones and conjugated carbonyl derivatives. This method allows for the synthesis of complex heterocycles under very mild conditions with good yields and selectivities. The data observed justifies a potential redox‐neutral photocatalytic pathway for the observed products.</description><subject>dipolar cycloadditions</subject><subject>heterocycles</subject><subject>isoxazolidines</subject><subject>photocatalysis</subject><subject>vinyl nitrones</subject><issn>2367-0932</issn><issn>2367-0932</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkM1KAzEUhYMoWGq3rvMCU5PMNMksZfCnULDQ6nbI5KdNmU5KklbHVR_BZ_RJnKGi7lzde_nOuQcOANcYjTFC5EbuohwTREh3MHYGBiSlLEF5Ss7_7JdgFMIGIYR5NsEoG4DDom3iWgcboDNwGtybeHe1VbbRARrvtnCxr0K0cR-1gi-2aevGRu96LBoFC9ds9ivRw0L4ynU8wIMVnTTYqtafx4-ZXa0jnK9ddFJEUbdd2BW4MKIOevQ9h-D5_m5ZPCazp4dpcTtLJOE5SzTBec445WKSMYooTivGsZCcsZxXGUmNUZlEVKfKZKaimaFYUWG0mEiuUpMOwfj0V3oXgtem3Hm7Fb4tMSr74sq-uPKnuM6QnwyvttbtP-qymC-LX-8XvE12lA</recordid><startdate>202303</startdate><enddate>202303</enddate><creator>Trieu, Phillip</creator><creator>Filkin, William H.</creator><creator>Pinarci, Ali</creator><creator>Tobias, Elisa M.</creator><creator>Madiu, Rufai</creator><creator>Dellosso, Brandon</creator><creator>Roldan, Justin</creator><creator>Das, Pulakesh</creator><creator>Austin, Brooke E.</creator><creator>Moura‐Letts, Gustavo</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8156-151X</orcidid></search><sort><creationdate>202303</creationdate><title>Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible‐Light Photocatalysis</title><author>Trieu, Phillip ; Filkin, William H. ; Pinarci, Ali ; Tobias, Elisa M. ; Madiu, Rufai ; Dellosso, Brandon ; Roldan, Justin ; Das, Pulakesh ; Austin, Brooke E. ; Moura‐Letts, Gustavo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2897-e21997868a54760613b781ac87798b423ffd4c06e3df4fb64f61d6afea5c8d3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>dipolar cycloadditions</topic><topic>heterocycles</topic><topic>isoxazolidines</topic><topic>photocatalysis</topic><topic>vinyl nitrones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trieu, Phillip</creatorcontrib><creatorcontrib>Filkin, William H.</creatorcontrib><creatorcontrib>Pinarci, Ali</creatorcontrib><creatorcontrib>Tobias, Elisa M.</creatorcontrib><creatorcontrib>Madiu, Rufai</creatorcontrib><creatorcontrib>Dellosso, Brandon</creatorcontrib><creatorcontrib>Roldan, Justin</creatorcontrib><creatorcontrib>Das, Pulakesh</creatorcontrib><creatorcontrib>Austin, Brooke E.</creatorcontrib><creatorcontrib>Moura‐Letts, Gustavo</creatorcontrib><collection>CrossRef</collection><jtitle>ChemPhotoChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Trieu, Phillip</au><au>Filkin, William H.</au><au>Pinarci, Ali</au><au>Tobias, Elisa M.</au><au>Madiu, Rufai</au><au>Dellosso, Brandon</au><au>Roldan, Justin</au><au>Das, Pulakesh</au><au>Austin, Brooke E.</au><au>Moura‐Letts, Gustavo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible‐Light Photocatalysis</atitle><jtitle>ChemPhotoChem</jtitle><date>2023-03</date><risdate>2023</risdate><volume>7</volume><issue>3</issue><epage>n/a</epage><issn>2367-0932</issn><eissn>2367-0932</eissn><abstract>Herein we report the first redox‐neutral visible‐light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible‐light‐promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox‐neutral pathway is proposed as the primary photoredox mechanism for this transformation.
Redox neutral pathway: This effort highlights the first highly stereoselective photocatalytic dipolar cycloaddition of vinyl nitrones and conjugated carbonyl derivatives. This method allows for the synthesis of complex heterocycles under very mild conditions with good yields and selectivities. The data observed justifies a potential redox‐neutral photocatalytic pathway for the observed products.</abstract><doi>10.1002/cptc.202200277</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8156-151X</orcidid></addata></record> |
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| source | Wiley Online Library All Journals |
| subjects | dipolar cycloadditions heterocycles isoxazolidines photocatalysis vinyl nitrones |
| title | Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible‐Light Photocatalysis |
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