Realizing an Aza Paternò–Büchi Reaction
Intramolecular atropselective aza Paternò–Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity (ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studi...
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| Veröffentlicht in: | Angewandte Chemie 2017-06, Vol.129 (25), p.7162-7167 |
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| container_end_page | 7167 |
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| container_issue | 25 |
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| container_title | Angewandte Chemie |
| container_volume | 129 |
| creator | Kumarasamy, Elango Kandappa, Sunil Kumar Raghunathan, Ramya Jockusch, Steffen Sivaguru, Jayaraman |
| description | Intramolecular atropselective aza Paternò–Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity (ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studies is provided that shed light into the reactivity of enamides leading to aza Paternò–Büchi reaction.
Eine intramolekulare Aza‐Paternò‐Büchi‐Reaktion zwischen atropisomeren Enamid‐ und Iminfunktionalitäten unter sensibilisierender Bestrahlung führt mit guten Ausbeuten und hohem Enantiomerenüberschuss zu Azetidinprodukten (siehe Schema). Der Reaktionsmechanismus wurde durch detaillierte photophysikalische und kinetische Studien erforscht. |
| doi_str_mv | 10.1002/ange.201702273 |
| format | Article |
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Eine intramolekulare Aza‐Paternò‐Büchi‐Reaktion zwischen atropisomeren Enamid‐ und Iminfunktionalitäten unter sensibilisierender Bestrahlung führt mit guten Ausbeuten und hohem Enantiomerenüberschuss zu Azetidinprodukten (siehe Schema). Der Reaktionsmechanismus wurde durch detaillierte photophysikalische und kinetische Studien erforscht.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201702273</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>[2+2]-Photocycloadditionen ; Asymmetrische Photoreaktionen ; Atropselektivität ; Aza-Paternò-Büchi-Reaktion ; Chemistry ; Imine ; Irradiation ; Isomerization ; Radiation ; Selectivity</subject><ispartof>Angewandte Chemie, 2017-06, Vol.129 (25), p.7162-7167</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2283-753e036c28ea3331bfe47d39e0fa4a8734b221e71151255d1b9e3b07434712443</citedby><cites>FETCH-LOGICAL-c2283-753e036c28ea3331bfe47d39e0fa4a8734b221e71151255d1b9e3b07434712443</cites><orcidid>0000-0002-7995-6894 ; 0000-0002-6750-4778 ; 0000-0003-0672-7369 ; 0000-0002-4592-5280 ; 0000-0002-0446-6903</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.201702273$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201702273$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Kumarasamy, Elango</creatorcontrib><creatorcontrib>Kandappa, Sunil Kumar</creatorcontrib><creatorcontrib>Raghunathan, Ramya</creatorcontrib><creatorcontrib>Jockusch, Steffen</creatorcontrib><creatorcontrib>Sivaguru, Jayaraman</creatorcontrib><title>Realizing an Aza Paternò–Büchi Reaction</title><title>Angewandte Chemie</title><description>Intramolecular atropselective aza Paternò–Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity (ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studies is provided that shed light into the reactivity of enamides leading to aza Paternò–Büchi reaction.
Eine intramolekulare Aza‐Paternò‐Büchi‐Reaktion zwischen atropisomeren Enamid‐ und Iminfunktionalitäten unter sensibilisierender Bestrahlung führt mit guten Ausbeuten und hohem Enantiomerenüberschuss zu Azetidinprodukten (siehe Schema). Der Reaktionsmechanismus wurde durch detaillierte photophysikalische und kinetische Studien erforscht.</description><subject>[2+2]-Photocycloadditionen</subject><subject>Asymmetrische Photoreaktionen</subject><subject>Atropselektivität</subject><subject>Aza-Paternò-Büchi-Reaktion</subject><subject>Chemistry</subject><subject>Imine</subject><subject>Irradiation</subject><subject>Isomerization</subject><subject>Radiation</subject><subject>Selectivity</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOw0AMQE8IJEphZY7EiBJs36WXjKUqBakChGA-XVKnpApJubRC7cQ_8CfMbP0TvoSUIBiZvLxnW0-IY4QAAejMllMOCFADkZY7ooMhoS91qHdFB0ApPyIV74uDup4BQI903BGnd2yLfJ2XU8-WXn9tvVu7YFdu3j9f3843H-lj7jVIusir8lDsZbao-ehndsXDxfB-cOmPb0ZXg_7YT4ki6etQMsheShFbKSUmGSs9kTFDZpWNtFQJEbJGDJHCcIJJzDIBraTSSErJrjhp985d9bzkemFm1dKVzUmDcfM3QfRNBS2VuqquHWdm7vIn61YGwWyDmG0Q8xukEeJWeMkLXv1Dm_71aPjnfgHJp2N4</recordid><startdate>20170612</startdate><enddate>20170612</enddate><creator>Kumarasamy, Elango</creator><creator>Kandappa, Sunil Kumar</creator><creator>Raghunathan, Ramya</creator><creator>Jockusch, Steffen</creator><creator>Sivaguru, Jayaraman</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/0000-0002-7995-6894</orcidid><orcidid>https://orcid.org/0000-0002-6750-4778</orcidid><orcidid>https://orcid.org/0000-0003-0672-7369</orcidid><orcidid>https://orcid.org/0000-0002-4592-5280</orcidid><orcidid>https://orcid.org/0000-0002-0446-6903</orcidid></search><sort><creationdate>20170612</creationdate><title>Realizing an Aza Paternò–Büchi Reaction</title><author>Kumarasamy, Elango ; Kandappa, Sunil Kumar ; Raghunathan, Ramya ; Jockusch, Steffen ; Sivaguru, Jayaraman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2283-753e036c28ea3331bfe47d39e0fa4a8734b221e71151255d1b9e3b07434712443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>[2+2]-Photocycloadditionen</topic><topic>Asymmetrische Photoreaktionen</topic><topic>Atropselektivität</topic><topic>Aza-Paternò-Büchi-Reaktion</topic><topic>Chemistry</topic><topic>Imine</topic><topic>Irradiation</topic><topic>Isomerization</topic><topic>Radiation</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumarasamy, Elango</creatorcontrib><creatorcontrib>Kandappa, Sunil Kumar</creatorcontrib><creatorcontrib>Raghunathan, Ramya</creatorcontrib><creatorcontrib>Jockusch, Steffen</creatorcontrib><creatorcontrib>Sivaguru, Jayaraman</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>Kumarasamy, Elango</au><au>Kandappa, Sunil Kumar</au><au>Raghunathan, Ramya</au><au>Jockusch, Steffen</au><au>Sivaguru, Jayaraman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Realizing an Aza Paternò–Büchi Reaction</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-06-12</date><risdate>2017</risdate><volume>129</volume><issue>25</issue><spage>7162</spage><epage>7167</epage><pages>7162-7167</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Intramolecular atropselective aza Paternò–Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity (ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studies is provided that shed light into the reactivity of enamides leading to aza Paternò–Büchi reaction.
Eine intramolekulare Aza‐Paternò‐Büchi‐Reaktion zwischen atropisomeren Enamid‐ und Iminfunktionalitäten unter sensibilisierender Bestrahlung führt mit guten Ausbeuten und hohem Enantiomerenüberschuss zu Azetidinprodukten (siehe Schema). Der Reaktionsmechanismus wurde durch detaillierte photophysikalische und kinetische Studien erforscht.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201702273</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-7995-6894</orcidid><orcidid>https://orcid.org/0000-0002-6750-4778</orcidid><orcidid>https://orcid.org/0000-0003-0672-7369</orcidid><orcidid>https://orcid.org/0000-0002-4592-5280</orcidid><orcidid>https://orcid.org/0000-0002-0446-6903</orcidid></addata></record> |
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| subjects | [2+2]-Photocycloadditionen Asymmetrische Photoreaktionen Atropselektivität Aza-Paternò-Büchi-Reaktion Chemistry Imine Irradiation Isomerization Radiation Selectivity |
| title | Realizing an Aza Paternò–Büchi Reaction |
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