Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening

Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening

An intramolecular cascade reaction consisting of a formal anti-carbopalladation terminated by the ring-opening of a cyclopropanol unit is presented. The products, which involve tetrasubstituted alkene units embedded in an oligocyclic ring system, are generated in moderate to excellent yield. The ope...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2018-11, Vol.20 (22), p.7266-7269
Hauptverfasser: Reding, Andreas, Jones, Peter G, Werz, Daniel B
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7269
container_issue 22
container_start_page 7266
container_title Organic letters
container_volume 20
creator Reding, Andreas
Jones, Peter G
Werz, Daniel B
description An intramolecular cascade reaction consisting of a formal anti-carbopalladation terminated by the ring-opening of a cyclopropanol unit is presented. The products, which involve tetrasubstituted alkene units embedded in an oligocyclic ring system, are generated in moderate to excellent yield. The opening of the cyclopropanol unit leads to a keto group in the γ-position to the emerging double bond.
doi_str_mv 10.1021/acs.orglett.8b03179
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2130802003</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2130802003</sourcerecordid><originalsourceid>FETCH-LOGICAL-a411t-a2a43750cbc1ad79016302970d306fa93eaa4bc3804e5bd6980fec2ba4d1aa183</originalsourceid><addsrcrecordid>eNp9kD1PwzAQhi0EoqXwC5BQRpa0ZzttkrGKKFSq1AXm6OI4VYpjFzsZIvHjcUjpyOKP83OvTw8hjxTmFBhdoHBzYw9Ktu08KYDTOL0iU7pkPIxhya4v5xVMyJ1zRwDqK-ktmXDgaZIkbEq-t7q12BglRafQBv6iXZihLYwYFo1tbXRgqsCD0mpUwVp99lq6oOgDDDJ0Aks5ABtjG_-Muq3HgBMqheVvwCLrhTIn62vaqGB_krrWh3tyU6Fy8uG8z8jH5uU9ewt3-9dttt6FGFHahsgw4vESRCEolnEKdMWBpTGUHFYVplwiRoXgCURyWZSrNIFKClZgVFJEmvAZeR5z_QBfnXRt3tROSD-dlqZzOaMcEmAA3KN8RIU1zllZ5SdbN2j7nEI-aM-99vysPT9r911P5w-6opHlpefPswcWIzB0H003iHT_Rv4Ae0iT9Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2130802003</pqid></control><display><type>article</type><title>Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening</title><source>ACS Publications</source><creator>Reding, Andreas ; Jones, Peter G ; Werz, Daniel B</creator><creatorcontrib>Reding, Andreas ; Jones, Peter G ; Werz, Daniel B</creatorcontrib><description>An intramolecular cascade reaction consisting of a formal anti-carbopalladation terminated by the ring-opening of a cyclopropanol unit is presented. The products, which involve tetrasubstituted alkene units embedded in an oligocyclic ring system, are generated in moderate to excellent yield. The opening of the cyclopropanol unit leads to a keto group in the γ-position to the emerging double bond.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.8b03179</identifier><identifier>PMID: 30398882</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2018-11, Vol.20 (22), p.7266-7269</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-a2a43750cbc1ad79016302970d306fa93eaa4bc3804e5bd6980fec2ba4d1aa183</citedby><cites>FETCH-LOGICAL-a411t-a2a43750cbc1ad79016302970d306fa93eaa4bc3804e5bd6980fec2ba4d1aa183</cites><orcidid>0000-0002-3973-2212</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.8b03179$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.8b03179$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30398882$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Reding, Andreas</creatorcontrib><creatorcontrib>Jones, Peter G</creatorcontrib><creatorcontrib>Werz, Daniel B</creatorcontrib><title>Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An intramolecular cascade reaction consisting of a formal anti-carbopalladation terminated by the ring-opening of a cyclopropanol unit is presented. The products, which involve tetrasubstituted alkene units embedded in an oligocyclic ring system, are generated in moderate to excellent yield. The opening of the cyclopropanol unit leads to a keto group in the γ-position to the emerging double bond.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kD1PwzAQhi0EoqXwC5BQRpa0ZzttkrGKKFSq1AXm6OI4VYpjFzsZIvHjcUjpyOKP83OvTw8hjxTmFBhdoHBzYw9Ktu08KYDTOL0iU7pkPIxhya4v5xVMyJ1zRwDqK-ktmXDgaZIkbEq-t7q12BglRafQBv6iXZihLYwYFo1tbXRgqsCD0mpUwVp99lq6oOgDDDJ0Aks5ABtjG_-Muq3HgBMqheVvwCLrhTIn62vaqGB_krrWh3tyU6Fy8uG8z8jH5uU9ewt3-9dttt6FGFHahsgw4vESRCEolnEKdMWBpTGUHFYVplwiRoXgCURyWZSrNIFKClZgVFJEmvAZeR5z_QBfnXRt3tROSD-dlqZzOaMcEmAA3KN8RIU1zllZ5SdbN2j7nEI-aM-99vysPT9r911P5w-6opHlpefPswcWIzB0H003iHT_Rv4Ae0iT9Q</recordid><startdate>20181116</startdate><enddate>20181116</enddate><creator>Reding, Andreas</creator><creator>Jones, Peter G</creator><creator>Werz, Daniel B</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3973-2212</orcidid></search><sort><creationdate>20181116</creationdate><title>Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening</title><author>Reding, Andreas ; Jones, Peter G ; Werz, Daniel B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-a2a43750cbc1ad79016302970d306fa93eaa4bc3804e5bd6980fec2ba4d1aa183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reding, Andreas</creatorcontrib><creatorcontrib>Jones, Peter G</creatorcontrib><creatorcontrib>Werz, Daniel B</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reding, Andreas</au><au>Jones, Peter G</au><au>Werz, Daniel B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2018-11-16</date><risdate>2018</risdate><volume>20</volume><issue>22</issue><spage>7266</spage><epage>7269</epage><pages>7266-7269</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An intramolecular cascade reaction consisting of a formal anti-carbopalladation terminated by the ring-opening of a cyclopropanol unit is presented. The products, which involve tetrasubstituted alkene units embedded in an oligocyclic ring system, are generated in moderate to excellent yield. The opening of the cyclopropanol unit leads to a keto group in the γ-position to the emerging double bond.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>30398882</pmid><doi>10.1021/acs.orglett.8b03179</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-3973-2212</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2018-11, Vol.20 (22), p.7266-7269
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2130802003
source ACS Publications
title Intramolecular trans-Carbocarbonation of Internal Alkynes by a Cascade of Formal anti-Carbopalladation/Cyclopropanol Opening
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T10%3A35%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Intramolecular%20trans-Carbocarbonation%20of%20Internal%20Alkynes%20by%20a%20Cascade%20of%20Formal%20anti-Carbopalladation/Cyclopropanol%20Opening&rft.jtitle=Organic%20letters&rft.au=Reding,%20Andreas&rft.date=2018-11-16&rft.volume=20&rft.issue=22&rft.spage=7266&rft.epage=7269&rft.pages=7266-7269&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.8b03179&rft_dat=%3Cproquest_cross%3E2130802003%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2130802003&rft_id=info:pmid/30398882&rfr_iscdi=true