Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes
The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α‐cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the o...
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| Veröffentlicht in: | Angewandte Chemie 2015-08, Vol.127 (33), p.9804-9808 |
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| container_issue | 33 |
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| container_title | Angewandte Chemie |
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| creator | Welin, Eric R. Warkentin, Alexander A. Conrad, Jay C. MacMillan, David W. C. |
| description | The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α‐cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (−)‐bursehernin.
Eine Kombination von Photoredoxkatalyse und Enaminkatalyse ermöglichte die Entwicklung einer enantioselektiven Cyanoalkylierung von Aldehyden. Mit dem synergetischen Katalyseverfahren können zwei äußerst vielseitige und zugleich orthogonale Funktionen miteinander gekuppelt werden. |
| doi_str_mv | 10.1002/ange.201503789 |
| format | Article |
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Eine Kombination von Photoredoxkatalyse und Enaminkatalyse ermöglichte die Entwicklung einer enantioselektiven Cyanoalkylierung von Aldehyden. Mit dem synergetischen Katalyseverfahren können zwei äußerst vielseitige und zugleich orthogonale Funktionen miteinander gekuppelt werden.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201503789</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehyde ; Aldehydes ; Alkylierung ; Arrays ; Catalysis ; Derivatives ; Joining ; Lignans ; Natural products ; Organokatalyse ; Photoredoxkatalyse ; Synthesis ; Totalsynthese</subject><ispartof>Angewandte Chemie, 2015-08, Vol.127 (33), p.9804-9808</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2059-4ddbe3b19a2afa029e446c793cf0cf4859adfc5fa9c6d9deb97fbed909fa66873</citedby><cites>FETCH-LOGICAL-c2059-4ddbe3b19a2afa029e446c793cf0cf4859adfc5fa9c6d9deb97fbed909fa66873</cites></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.201503789$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201503789$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Welin, Eric R.</creatorcontrib><creatorcontrib>Warkentin, Alexander A.</creatorcontrib><creatorcontrib>Conrad, Jay C.</creatorcontrib><creatorcontrib>MacMillan, David W. C.</creatorcontrib><title>Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α‐cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (−)‐bursehernin.
Eine Kombination von Photoredoxkatalyse und Enaminkatalyse ermöglichte die Entwicklung einer enantioselektiven Cyanoalkylierung von Aldehyden. Mit dem synergetischen Katalyseverfahren können zwei äußerst vielseitige und zugleich orthogonale Funktionen miteinander gekuppelt werden.</description><subject>Aldehyde</subject><subject>Aldehydes</subject><subject>Alkylierung</subject><subject>Arrays</subject><subject>Catalysis</subject><subject>Derivatives</subject><subject>Joining</subject><subject>Lignans</subject><subject>Natural products</subject><subject>Organokatalyse</subject><subject>Photoredoxkatalyse</subject><subject>Synthesis</subject><subject>Totalsynthese</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkc1O3DAUhS1UJKbAlrWX3WTqOD-Ou4tGwxRpBAhRlZ11Y1_PpDjx1A4teQQep30QnomgaVF3XV3p6PvO4lxCzlI2TxnjH6Hf4JyztGCZqOQBmaUFT5NMFOIdmTGW50nFc3lE3sf4jTFWciFn5GnZQz-0PqJDPbQ_kD7_Smp3PzqY0p56S2tncDsajLQZ6fXWDz6g8Y_0Kmyg9xoGcGNs4yd6A7vW0FprjJEOfmIhdKD9bjsZ9DzApsN-iNQG39Hn38linHz4235CDi24iKd_7jH5cr68XXxO1leri0W9TjRnhUxyYxrMmlQCBwuMS8zzUguZacu0zatCgrG6sCB1aaTBRgrboJFMWijLSmTH5MO-dxf89weMg-raqNE56NE_RJWKqbDKeJlP6HyP6uBjDGjVLrQdhFGlTL1url43V2-bT4LcCz9bh-N_aFVfrpb_usnebeOAj28uhHtViumL6uvlShWL9R27q27UbfYCb8ma-w</recordid><startdate>20150810</startdate><enddate>20150810</enddate><creator>Welin, Eric R.</creator><creator>Warkentin, Alexander A.</creator><creator>Conrad, Jay C.</creator><creator>MacMillan, David W. C.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150810</creationdate><title>Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes</title><author>Welin, Eric R. ; Warkentin, Alexander A. ; Conrad, Jay C. ; MacMillan, David W. C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2059-4ddbe3b19a2afa029e446c793cf0cf4859adfc5fa9c6d9deb97fbed909fa66873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Aldehyde</topic><topic>Aldehydes</topic><topic>Alkylierung</topic><topic>Arrays</topic><topic>Catalysis</topic><topic>Derivatives</topic><topic>Joining</topic><topic>Lignans</topic><topic>Natural products</topic><topic>Organokatalyse</topic><topic>Photoredoxkatalyse</topic><topic>Synthesis</topic><topic>Totalsynthese</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Welin, Eric R.</creatorcontrib><creatorcontrib>Warkentin, Alexander A.</creatorcontrib><creatorcontrib>Conrad, Jay C.</creatorcontrib><creatorcontrib>MacMillan, David W. C.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Welin, Eric R.</au><au>Warkentin, Alexander A.</au><au>Conrad, Jay C.</au><au>MacMillan, David W. C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-08-10</date><risdate>2015</risdate><volume>127</volume><issue>33</issue><spage>9804</spage><epage>9808</epage><pages>9804-9808</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α‐cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (−)‐bursehernin.
Eine Kombination von Photoredoxkatalyse und Enaminkatalyse ermöglichte die Entwicklung einer enantioselektiven Cyanoalkylierung von Aldehyden. Mit dem synergetischen Katalyseverfahren können zwei äußerst vielseitige und zugleich orthogonale Funktionen miteinander gekuppelt werden.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201503789</doi><tpages>5</tpages></addata></record> |
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| subjects | Aldehyde Aldehydes Alkylierung Arrays Catalysis Derivatives Joining Lignans Natural products Organokatalyse Photoredoxkatalyse Synthesis Totalsynthese |
| title | Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes |
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