Asymmetric Vinylogous Diels-Alder Reactions Catalyzed by a Chiral Phosphoric Acid
An unprecedented way to extend the synthetic utility of the Diels–Alder reaction to include a vinylogous reactivity space is described. A commercially available chiral phosphoric acid catalyst effectively activates cyclic 2,4‐dienones towards a vinylogous [4+2] cycloaddition with 2‐vinylindoles, whi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-03, Vol.53 (11), p.2997-3000 |
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| creator | Tian, Xu Hofmann, Nora Melchiorre, Paolo |
| description | An unprecedented way to extend the synthetic utility of the Diels–Alder reaction to include a vinylogous reactivity space is described. A commercially available chiral phosphoric acid catalyst effectively activates cyclic 2,4‐dienones towards a vinylogous [4+2] cycloaddition with 2‐vinylindoles, which leads to stereochemically dense tetrahydrocarbazoles. The reaction proceeds with a high level of remote stereocontrol and exclusive chemoselectivity for the more distant double bond of the dienone.
Further and further: A vinylogous Diels–Alder reaction that is catalyzed by a commercially available chiral phosphoric acid has been developed. A range of structurally diverse complex tetrahydrocarbazoles were obtained in high chemical yields and with excellent stereoselectivity. It was thus demonstrated that the synthetic utility of the Diels–Alder reaction can be extended to include a vinylogous reactivity space. |
| doi_str_mv | 10.1002/anie.201310487 |
| format | Article |
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Further and further: A vinylogous Diels–Alder reaction that is catalyzed by a commercially available chiral phosphoric acid has been developed. A range of structurally diverse complex tetrahydrocarbazoles were obtained in high chemical yields and with excellent stereoselectivity. It was thus demonstrated that the synthetic utility of the Diels–Alder reaction can be extended to include a vinylogous reactivity space.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201310487</identifier><identifier>PMID: 24504630</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>asymmetric catalysis ; Asymmetry ; Brønsted acids ; Catalysts ; Chemical industry ; Cycloaddition ; Diels-Alder reactions ; Level (quantity) ; organocatalysis ; Phosphoric acid ; Stereoselectivity ; synthetic methods ; Utilities</subject><ispartof>Angewandte Chemie International Edition, 2014-03, Vol.53 (11), p.2997-3000</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5477-333c7fa7274b5111cb5091e859da2c7b7e56509e908367aad7e402a51bb0e7c63</citedby><cites>FETCH-LOGICAL-c5477-333c7fa7274b5111cb5091e859da2c7b7e56509e908367aad7e402a51bb0e7c63</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.201310487$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201310487$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24504630$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tian, Xu</creatorcontrib><creatorcontrib>Hofmann, Nora</creatorcontrib><creatorcontrib>Melchiorre, Paolo</creatorcontrib><title>Asymmetric Vinylogous Diels-Alder Reactions Catalyzed by a Chiral Phosphoric Acid</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>An unprecedented way to extend the synthetic utility of the Diels–Alder reaction to include a vinylogous reactivity space is described. A commercially available chiral phosphoric acid catalyst effectively activates cyclic 2,4‐dienones towards a vinylogous [4+2] cycloaddition with 2‐vinylindoles, which leads to stereochemically dense tetrahydrocarbazoles. The reaction proceeds with a high level of remote stereocontrol and exclusive chemoselectivity for the more distant double bond of the dienone.
Further and further: A vinylogous Diels–Alder reaction that is catalyzed by a commercially available chiral phosphoric acid has been developed. A range of structurally diverse complex tetrahydrocarbazoles were obtained in high chemical yields and with excellent stereoselectivity. It was thus demonstrated that the synthetic utility of the Diels–Alder reaction can be extended to include a vinylogous reactivity space.</description><subject>asymmetric catalysis</subject><subject>Asymmetry</subject><subject>Brønsted acids</subject><subject>Catalysts</subject><subject>Chemical industry</subject><subject>Cycloaddition</subject><subject>Diels-Alder reactions</subject><subject>Level (quantity)</subject><subject>organocatalysis</subject><subject>Phosphoric acid</subject><subject>Stereoselectivity</subject><subject>synthetic methods</subject><subject>Utilities</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkU1v1DAQhiMEoqVw5YgiceGSxd-THKO0WypV5RuOluPMsi5OsthZQfj1ONqyQlx6Gmv0vI80frPsOSUrSgh7bQaHK0Yop0SU8CA7pZLRggPwh-ktOC-glPQkexLjbeLLkqjH2QkTkgjFyWn2vo5z3-MUnM2_uGH247dxH_Nzhz4Wte8w5B_Q2MmNQ8wbMxk__8Yub-fc5M3WBePzd9sx7rbjYqit655mjzbGR3x2N8-yz-uLT82b4vrt5VVTXxdWCoCCc25hY4CBaCWl1LaSVBRLWXWGWWgBpUobrEjJFRjTAQrCjKRtSxCs4mfZq4N3F8Yfe4yT7l206L0ZMJ2gKRBSlSVLf3AvKolkUlG-WF_-h96O-zCkQxZKKCpB0kStDpQNY4wBN3oXXG_CrCnRSy966UUfe0mBF3fafdtjd8T_FpGA6gD8dB7ne3S6vrm6-FdeHLIuTvjrmDXhu1bAQeqvN5caPjZrtVZcC_4H83SmEA</recordid><startdate>20140310</startdate><enddate>20140310</enddate><creator>Tian, Xu</creator><creator>Hofmann, Nora</creator><creator>Melchiorre, Paolo</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</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><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140310</creationdate><title>Asymmetric Vinylogous Diels-Alder Reactions Catalyzed by a Chiral Phosphoric Acid</title><author>Tian, Xu ; Hofmann, Nora ; Melchiorre, Paolo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5477-333c7fa7274b5111cb5091e859da2c7b7e56509e908367aad7e402a51bb0e7c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>asymmetric catalysis</topic><topic>Asymmetry</topic><topic>Brønsted acids</topic><topic>Catalysts</topic><topic>Chemical industry</topic><topic>Cycloaddition</topic><topic>Diels-Alder reactions</topic><topic>Level (quantity)</topic><topic>organocatalysis</topic><topic>Phosphoric acid</topic><topic>Stereoselectivity</topic><topic>synthetic methods</topic><topic>Utilities</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tian, Xu</creatorcontrib><creatorcontrib>Hofmann, Nora</creatorcontrib><creatorcontrib>Melchiorre, Paolo</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><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tian, Xu</au><au>Hofmann, Nora</au><au>Melchiorre, Paolo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Vinylogous Diels-Alder Reactions Catalyzed by a Chiral Phosphoric Acid</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-03-10</date><risdate>2014</risdate><volume>53</volume><issue>11</issue><spage>2997</spage><epage>3000</epage><pages>2997-3000</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>An unprecedented way to extend the synthetic utility of the Diels–Alder reaction to include a vinylogous reactivity space is described. A commercially available chiral phosphoric acid catalyst effectively activates cyclic 2,4‐dienones towards a vinylogous [4+2] cycloaddition with 2‐vinylindoles, which leads to stereochemically dense tetrahydrocarbazoles. The reaction proceeds with a high level of remote stereocontrol and exclusive chemoselectivity for the more distant double bond of the dienone.
Further and further: A vinylogous Diels–Alder reaction that is catalyzed by a commercially available chiral phosphoric acid has been developed. A range of structurally diverse complex tetrahydrocarbazoles were obtained in high chemical yields and with excellent stereoselectivity. It was thus demonstrated that the synthetic utility of the Diels–Alder reaction can be extended to include a vinylogous reactivity space.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24504630</pmid><doi>10.1002/anie.201310487</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record> |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | asymmetric catalysis Asymmetry Brønsted acids Catalysts Chemical industry Cycloaddition Diels-Alder reactions Level (quantity) organocatalysis Phosphoric acid Stereoselectivity synthetic methods Utilities |
| title | Asymmetric Vinylogous Diels-Alder Reactions Catalyzed by a Chiral Phosphoric Acid |
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