Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts
A highly enantioselective rhodium(I)‐catalyzed dearomative arylation or alkenylation of easily available N‐alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99 % ee. This reaction tolerates a wide range of functional...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-03, Vol.55 (11), p.3776-3780 |
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| creator | Wang, Yan Liu, Yunlong Zhang, Dongdong Wei, Hao Shi, Min Wang, Feijun |
| description | A highly enantioselective rhodium(I)‐catalyzed dearomative arylation or alkenylation of easily available N‐alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99 % ee. This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.
Rings made simple: The title reaction proceeds with readily available quinolines and has been developed to provide a practical way to furnish enantiopure dihydroquinolines. This method was successfully applied in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine. |
| doi_str_mv | 10.1002/anie.201511663 |
| format | Article |
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Rings made simple: The title reaction proceeds with readily available quinolines and has been developed to provide a practical way to furnish enantiopure dihydroquinolines. This method was successfully applied in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201511663</identifier><identifier>PMID: 26879692</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Asymmetric synthesis ; Biocompatibility ; boron ; Catalysis ; Chemical synthesis ; Enantiomers ; Functional groups ; heterocycles ; nucleophilic addition ; Quinoline ; Rhodium ; Salts ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2016-03, Vol.55 (11), p.3776-3780</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6823-5ff86c79df8a6586a828ccb7173fbd888022ede7f596bee59739f2a604a4ac133</citedby><cites>FETCH-LOGICAL-c6823-5ff86c79df8a6586a828ccb7173fbd888022ede7f596bee59739f2a604a4ac133</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%2Fanie.201511663$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201511663$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26879692$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Yan</creatorcontrib><creatorcontrib>Liu, Yunlong</creatorcontrib><creatorcontrib>Zhang, Dongdong</creatorcontrib><creatorcontrib>Wei, Hao</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><creatorcontrib>Wang, Feijun</creatorcontrib><title>Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A highly enantioselective rhodium(I)‐catalyzed dearomative arylation or alkenylation of easily available N‐alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99 % ee. This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.
Rings made simple: The title reaction proceeds with readily available quinolines and has been developed to provide a practical way to furnish enantiopure dihydroquinolines. This method was successfully applied in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.</description><subject>Asymmetric synthesis</subject><subject>Biocompatibility</subject><subject>boron</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Enantiomers</subject><subject>Functional groups</subject><subject>heterocycles</subject><subject>nucleophilic addition</subject><subject>Quinoline</subject><subject>Rhodium</subject><subject>Salts</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkc1vEzEQxS0EoqVw5YhW4sJlw9qOx_YxSkNbVJWvop6Q5eyOhVvvuti7QPjrcUiJEAc4zYz8e09PfoQ8pc2MNg17aQePM9ZQQSkAv0cOqWC05lLy-2Wfc15LJegBeZTzdeGVauAhOWCgpAbNDsmn1WCH0ceMAdvRf8Xq_efY-amvl3a0YfMDu-oYbYq9_fW6SJtQtjhUMVWLcIPD_nbVu8kPMfihyKsPNoz5MXngbMj45G4ekY-vVpfL0_r8zcnZcnFet6AYr4VzClqpO6csCAVWMdW2a0kld-tOldCMYYfSCQ1rRKEl145ZaOZ2blvK-RF5sfO9TfHLhHk0vc8thmAHjFM2VILWigkQBX3-F3odpzSUdIbqBgAolG_7FyVBAaUMttRsR7Up5pzQmdvke5s2hjZmW4_Z1mP29RTBszvbad1jt8d_91EAvQO--YCb_9iZxcXZ6k_zeqf1ecTve61NNwYkl8JcXZyU9KfLt_L1lbnkPwE0rKsQ</recordid><startdate>20160307</startdate><enddate>20160307</enddate><creator>Wang, Yan</creator><creator>Liu, Yunlong</creator><creator>Zhang, Dongdong</creator><creator>Wei, Hao</creator><creator>Shi, Min</creator><creator>Wang, Feijun</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160307</creationdate><title>Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts</title><author>Wang, Yan ; Liu, Yunlong ; Zhang, Dongdong ; Wei, Hao ; Shi, Min ; Wang, Feijun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6823-5ff86c79df8a6586a828ccb7173fbd888022ede7f596bee59739f2a604a4ac133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Asymmetric synthesis</topic><topic>Biocompatibility</topic><topic>boron</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Enantiomers</topic><topic>Functional groups</topic><topic>heterocycles</topic><topic>nucleophilic addition</topic><topic>Quinoline</topic><topic>Rhodium</topic><topic>Salts</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Yan</creatorcontrib><creatorcontrib>Liu, Yunlong</creatorcontrib><creatorcontrib>Zhang, Dongdong</creatorcontrib><creatorcontrib>Wei, Hao</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><creatorcontrib>Wang, Feijun</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Yan</au><au>Liu, Yunlong</au><au>Zhang, Dongdong</au><au>Wei, Hao</au><au>Shi, Min</au><au>Wang, Feijun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-03-07</date><risdate>2016</risdate><volume>55</volume><issue>11</issue><spage>3776</spage><epage>3780</epage><pages>3776-3780</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A highly enantioselective rhodium(I)‐catalyzed dearomative arylation or alkenylation of easily available N‐alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99 % ee. This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.
Rings made simple: The title reaction proceeds with readily available quinolines and has been developed to provide a practical way to furnish enantiopure dihydroquinolines. This method was successfully applied in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26879692</pmid><doi>10.1002/anie.201511663</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Asymmetric synthesis Biocompatibility boron Catalysis Chemical synthesis Enantiomers Functional groups heterocycles nucleophilic addition Quinoline Rhodium Salts total synthesis |
| title | Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts |
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