Gold-catalyzed [4+1]-annulation reactions between anthranils and 4-methoxy-1,2-dienyl-5-ynes involving a 1,2-allene shift
Gold-catalyzed [4+1]-annulations of 4-methoxy-1,2-dienyl-5-ynes with anthranils are described. The mechanism of these annulations involves nitrene formation of α-imino gold carbenes that undergo a 1,2-allene shift to form (pyrrol-2-yl) methylgold intermediates. With allenyl ester substrates, these g...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2019-02, Vol.55 (13), p.1979-1982 |
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container_end_page | 1982 |
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container_issue | 13 |
container_start_page | 1979 |
container_title | Chemical communications (Cambridge, England) |
container_volume | 55 |
creator | Hsieh, Hsiang-Chu Tan, Kuo-Chen Kulandai Raj, Antony Sekar Liu, Rai-Shung |
description | Gold-catalyzed [4+1]-annulations of 4-methoxy-1,2-dienyl-5-ynes with anthranils are described. The mechanism of these annulations involves nitrene formation of α-imino gold carbenes that undergo a 1,2-allene shift to form (pyrrol-2-yl) methylgold intermediates. With allenyl ester substrates, these gold intermediates become enolate species to enable intramolecular aldol reactions to form useful pyrrolo[1,2-
a
]quinoline derivatives.
Gold catalyzed [4+1]-annulations of 4-methoxy-1,2-dien-5-ynes with anthranils are described; the reaction mechanism involves initial formation of α-imino gold carbenes, followed by a subsequent 1,2-allene shift. |
doi_str_mv | 10.1039/c8cc09082c |
format | Article |
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a
]quinoline derivatives.
Gold catalyzed [4+1]-annulations of 4-methoxy-1,2-dien-5-ynes with anthranils are described; the reaction mechanism involves initial formation of α-imino gold carbenes, followed by a subsequent 1,2-allene shift.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c8cc09082c</identifier><identifier>PMID: 30687860</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Allene ; Carbenes ; Chemical reactions ; Crystallography ; Gold ; Organic chemistry ; Quinoline ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2019-02, Vol.55 (13), p.1979-1982</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-5f4385cf577f5bf5cddda3698e3b0d654a71af69deff3a3e211fef96bfbe72163</citedby><cites>FETCH-LOGICAL-c337t-5f4385cf577f5bf5cddda3698e3b0d654a71af69deff3a3e211fef96bfbe72163</cites><orcidid>0000-0002-2011-8124</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30687860$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hsieh, Hsiang-Chu</creatorcontrib><creatorcontrib>Tan, Kuo-Chen</creatorcontrib><creatorcontrib>Kulandai Raj, Antony Sekar</creatorcontrib><creatorcontrib>Liu, Rai-Shung</creatorcontrib><title>Gold-catalyzed [4+1]-annulation reactions between anthranils and 4-methoxy-1,2-dienyl-5-ynes involving a 1,2-allene shift</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Gold-catalyzed [4+1]-annulations of 4-methoxy-1,2-dienyl-5-ynes with anthranils are described. The mechanism of these annulations involves nitrene formation of α-imino gold carbenes that undergo a 1,2-allene shift to form (pyrrol-2-yl) methylgold intermediates. With allenyl ester substrates, these gold intermediates become enolate species to enable intramolecular aldol reactions to form useful pyrrolo[1,2-
a
]quinoline derivatives.
Gold catalyzed [4+1]-annulations of 4-methoxy-1,2-dien-5-ynes with anthranils are described; the reaction mechanism involves initial formation of α-imino gold carbenes, followed by a subsequent 1,2-allene shift.</description><subject>Aldehydes</subject><subject>Allene</subject><subject>Carbenes</subject><subject>Chemical reactions</subject><subject>Crystallography</subject><subject>Gold</subject><subject>Organic chemistry</subject><subject>Quinoline</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LHTEUhkOx1I92070ScCPW2HxMJpmlDGoFwU0LBSlDJjnpHcnNaDJjHX-9c71WwbM5L7wPhwMPQl8ZPWZUVN-ttpZWVHP7AW0xURZEFvr3xirLiihRyE20nfMNnYdJ_QltClpqpUu6habzPjhizWDC9AgOXxff2B9iYhyDGbo-4gTGrkLGLQz_ACI2cVgkE7uQ5-hwQZYwLPqHibAjTlwHcQpEkilCxl2878N9F_9ig1etCQEi4Lzo_PAZffQmZPjysnfQr7PTn_UPcnl1flGfXBIrhBqI9IXQ0nqplJetl9Y5Z0RZaRAtdaUsjGLGl5UD74URwBnz4Kuy9S0ozkqxgw7Wd29TfzdCHpplly2EYCL0Y244U1UhFJV0RvffoTf9mOL8XcM5o7rikvOZOlxTNvU5J_DNbeqWJk0No81KSFPrun4WUs_w3svJsV2Ce0X_G5iB3TWQsn1t34yKJwPFj6c</recordid><startdate>20190207</startdate><enddate>20190207</enddate><creator>Hsieh, Hsiang-Chu</creator><creator>Tan, Kuo-Chen</creator><creator>Kulandai Raj, Antony Sekar</creator><creator>Liu, Rai-Shung</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2011-8124</orcidid></search><sort><creationdate>20190207</creationdate><title>Gold-catalyzed [4+1]-annulation reactions between anthranils and 4-methoxy-1,2-dienyl-5-ynes involving a 1,2-allene shift</title><author>Hsieh, Hsiang-Chu ; Tan, Kuo-Chen ; Kulandai Raj, Antony Sekar ; Liu, Rai-Shung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-5f4385cf577f5bf5cddda3698e3b0d654a71af69deff3a3e211fef96bfbe72163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aldehydes</topic><topic>Allene</topic><topic>Carbenes</topic><topic>Chemical reactions</topic><topic>Crystallography</topic><topic>Gold</topic><topic>Organic chemistry</topic><topic>Quinoline</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hsieh, Hsiang-Chu</creatorcontrib><creatorcontrib>Tan, Kuo-Chen</creatorcontrib><creatorcontrib>Kulandai Raj, Antony Sekar</creatorcontrib><creatorcontrib>Liu, Rai-Shung</creatorcontrib><collection>PubMed</collection><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><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hsieh, Hsiang-Chu</au><au>Tan, Kuo-Chen</au><au>Kulandai Raj, Antony Sekar</au><au>Liu, Rai-Shung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gold-catalyzed [4+1]-annulation reactions between anthranils and 4-methoxy-1,2-dienyl-5-ynes involving a 1,2-allene shift</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2019-02-07</date><risdate>2019</risdate><volume>55</volume><issue>13</issue><spage>1979</spage><epage>1982</epage><pages>1979-1982</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Gold-catalyzed [4+1]-annulations of 4-methoxy-1,2-dienyl-5-ynes with anthranils are described. The mechanism of these annulations involves nitrene formation of α-imino gold carbenes that undergo a 1,2-allene shift to form (pyrrol-2-yl) methylgold intermediates. With allenyl ester substrates, these gold intermediates become enolate species to enable intramolecular aldol reactions to form useful pyrrolo[1,2-
a
]quinoline derivatives.
Gold catalyzed [4+1]-annulations of 4-methoxy-1,2-dien-5-ynes with anthranils are described; the reaction mechanism involves initial formation of α-imino gold carbenes, followed by a subsequent 1,2-allene shift.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30687860</pmid><doi>10.1039/c8cc09082c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-2011-8124</orcidid></addata></record> |
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language | eng |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Aldehydes Allene Carbenes Chemical reactions Crystallography Gold Organic chemistry Quinoline Substrates |
title | Gold-catalyzed [4+1]-annulation reactions between anthranils and 4-methoxy-1,2-dienyl-5-ynes involving a 1,2-allene shift |
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