Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center
Herein, the first use of trifluoromethyl-substituted enynes/enediynes as non-classical electron-deficient olefins for phosphine-catalyzed [3 + 2] cycloaddition with allenoates is reported. This reaction occurs with excellent regioselectivity under mild conditions, affording alkyne- and diyne-tethere...
Gespeichert in:
| Veröffentlicht in: | Organic chemistry frontiers an international journal of organic chemistry 2020-11, Vol.7 (21), p.3399-3405 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3405 |
|---|---|
| container_issue | 21 |
| container_start_page | 3399 |
| container_title | Organic chemistry frontiers an international journal of organic chemistry |
| container_volume | 7 |
| creator | Shu-Jie, Chen Guo-Shu, Chen Jia-Wei, Zhang Zhao-Dong, Li Yu-Lei, Zhao Yun-Lin, Liu |
| description | Herein, the first use of trifluoromethyl-substituted enynes/enediynes as non-classical electron-deficient olefins for phosphine-catalyzed [3 + 2] cycloaddition with allenoates is reported. This reaction occurs with excellent regioselectivity under mild conditions, affording alkyne- and diyne-tethered cyclopentene derivatives containing a CF3-substituted quaternary carbon center in moderate to good yields. |
| doi_str_mv | 10.1039/d0qo00807a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_journals_2454584271</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2454584271</sourcerecordid><originalsourceid>FETCH-LOGICAL-p183t-6066672e84271aa610405023e0680f2913152a7c7e34804a5d6761ba1db59d853</originalsourceid><addsrcrecordid>eNpNjsFKw0AURYMoWGo3fsGAS4l9M5OZpO6kWBUKutCVSHmZvJgpcabNTJD4T_6jrXXh6t7FPYebJOccrjjI2bSCrQcoIMejZCRAiTTjHI7_9dNkEsIaALhQGlQ-Sr6fGh82jXWUGozYDl9UsVfJLpl4Y2YwrceqstF6F5ivWexs3fa-8x8Um6Fl5AZHYUqOKrtv7NPGhmHbkvMYKVwzNIZCYNEfbBtykfZD411E66x7Z8jmC5mGvgzRxj7uDmz7Hdw57AZmsCu9Y2bPdWfJSY1toMlfjpOXxe3z_D5dPt49zG-W6YYXMqYatNa5oCITOUfUHDJQICSBLqAWMy65EpibnGRWQIaq0rnmJfKqVLOqUHKcXBy8m85vewpxtfb97k8bViJTmfoVyx-N_XL5</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2454584271</pqid></control><display><type>article</type><title>Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Shu-Jie, Chen ; Guo-Shu, Chen ; Jia-Wei, Zhang ; Zhao-Dong, Li ; Yu-Lei, Zhao ; Yun-Lin, Liu</creator><creatorcontrib>Shu-Jie, Chen ; Guo-Shu, Chen ; Jia-Wei, Zhang ; Zhao-Dong, Li ; Yu-Lei, Zhao ; Yun-Lin, Liu</creatorcontrib><description>Herein, the first use of trifluoromethyl-substituted enynes/enediynes as non-classical electron-deficient olefins for phosphine-catalyzed [3 + 2] cycloaddition with allenoates is reported. This reaction occurs with excellent regioselectivity under mild conditions, affording alkyne- and diyne-tethered cyclopentene derivatives containing a CF3-substituted quaternary carbon center in moderate to good yields.</description><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/d0qo00807a</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Alkenes ; Alkynes ; Carbon ; Crystallography ; Cycloaddition ; Cyclopentene ; Enediynes ; Organic chemistry ; Phosphine ; Phosphines ; Regioselectivity ; Substitutes</subject><ispartof>Organic chemistry frontiers an international journal of organic chemistry, 2020-11, Vol.7 (21), p.3399-3405</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Shu-Jie, Chen</creatorcontrib><creatorcontrib>Guo-Shu, Chen</creatorcontrib><creatorcontrib>Jia-Wei, Zhang</creatorcontrib><creatorcontrib>Zhao-Dong, Li</creatorcontrib><creatorcontrib>Yu-Lei, Zhao</creatorcontrib><creatorcontrib>Yun-Lin, Liu</creatorcontrib><title>Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center</title><title>Organic chemistry frontiers an international journal of organic chemistry</title><description>Herein, the first use of trifluoromethyl-substituted enynes/enediynes as non-classical electron-deficient olefins for phosphine-catalyzed [3 + 2] cycloaddition with allenoates is reported. This reaction occurs with excellent regioselectivity under mild conditions, affording alkyne- and diyne-tethered cyclopentene derivatives containing a CF3-substituted quaternary carbon center in moderate to good yields.</description><subject>Alkenes</subject><subject>Alkynes</subject><subject>Carbon</subject><subject>Crystallography</subject><subject>Cycloaddition</subject><subject>Cyclopentene</subject><subject>Enediynes</subject><subject>Organic chemistry</subject><subject>Phosphine</subject><subject>Phosphines</subject><subject>Regioselectivity</subject><subject>Substitutes</subject><issn>2052-4110</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpNjsFKw0AURYMoWGo3fsGAS4l9M5OZpO6kWBUKutCVSHmZvJgpcabNTJD4T_6jrXXh6t7FPYebJOccrjjI2bSCrQcoIMejZCRAiTTjHI7_9dNkEsIaALhQGlQ-Sr6fGh82jXWUGozYDl9UsVfJLpl4Y2YwrceqstF6F5ivWexs3fa-8x8Um6Fl5AZHYUqOKrtv7NPGhmHbkvMYKVwzNIZCYNEfbBtykfZD411E66x7Z8jmC5mGvgzRxj7uDmz7Hdw57AZmsCu9Y2bPdWfJSY1toMlfjpOXxe3z_D5dPt49zG-W6YYXMqYatNa5oCITOUfUHDJQICSBLqAWMy65EpibnGRWQIaq0rnmJfKqVLOqUHKcXBy8m85vewpxtfb97k8bViJTmfoVyx-N_XL5</recordid><startdate>20201107</startdate><enddate>20201107</enddate><creator>Shu-Jie, Chen</creator><creator>Guo-Shu, Chen</creator><creator>Jia-Wei, Zhang</creator><creator>Zhao-Dong, Li</creator><creator>Yu-Lei, Zhao</creator><creator>Yun-Lin, Liu</creator><general>Royal Society of Chemistry</general><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope></search><sort><creationdate>20201107</creationdate><title>Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center</title><author>Shu-Jie, Chen ; Guo-Shu, Chen ; Jia-Wei, Zhang ; Zhao-Dong, Li ; Yu-Lei, Zhao ; Yun-Lin, Liu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p183t-6066672e84271aa610405023e0680f2913152a7c7e34804a5d6761ba1db59d853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkenes</topic><topic>Alkynes</topic><topic>Carbon</topic><topic>Crystallography</topic><topic>Cycloaddition</topic><topic>Cyclopentene</topic><topic>Enediynes</topic><topic>Organic chemistry</topic><topic>Phosphine</topic><topic>Phosphines</topic><topic>Regioselectivity</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shu-Jie, Chen</creatorcontrib><creatorcontrib>Guo-Shu, Chen</creatorcontrib><creatorcontrib>Jia-Wei, Zhang</creatorcontrib><creatorcontrib>Zhao-Dong, Li</creatorcontrib><creatorcontrib>Yu-Lei, Zhao</creatorcontrib><creatorcontrib>Yun-Lin, Liu</creatorcontrib><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shu-Jie, Chen</au><au>Guo-Shu, Chen</au><au>Jia-Wei, Zhang</au><au>Zhao-Dong, Li</au><au>Yu-Lei, Zhao</au><au>Yun-Lin, Liu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center</atitle><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle><date>2020-11-07</date><risdate>2020</risdate><volume>7</volume><issue>21</issue><spage>3399</spage><epage>3405</epage><pages>3399-3405</pages><issn>2052-4110</issn><eissn>2052-4110</eissn><abstract>Herein, the first use of trifluoromethyl-substituted enynes/enediynes as non-classical electron-deficient olefins for phosphine-catalyzed [3 + 2] cycloaddition with allenoates is reported. This reaction occurs with excellent regioselectivity under mild conditions, affording alkyne- and diyne-tethered cyclopentene derivatives containing a CF3-substituted quaternary carbon center in moderate to good yields.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0qo00807a</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4110 |
| ispartof | Organic chemistry frontiers an international journal of organic chemistry, 2020-11, Vol.7 (21), p.3399-3405 |
| issn | 2052-4110 2052-4110 |
| language | eng |
| recordid | cdi_proquest_journals_2454584271 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Alkenes Alkynes Carbon Crystallography Cycloaddition Cyclopentene Enediynes Organic chemistry Phosphine Phosphines Regioselectivity Substitutes |
| title | Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T07%3A48%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Phosphine-catalyzed%20%5B3%20+%202%5D%20cycloadditions%20of%20trifluoromethyl%20enynes/enediynes%20with%20allenoates:%20access%20to%20cyclopentenes%20containing%20a%20CF3-substituted%20quaternary%20carbon%20center&rft.jtitle=Organic%20chemistry%20frontiers%20an%20international%20journal%20of%20organic%20chemistry&rft.au=Shu-Jie,%20Chen&rft.date=2020-11-07&rft.volume=7&rft.issue=21&rft.spage=3399&rft.epage=3405&rft.pages=3399-3405&rft.issn=2052-4110&rft.eissn=2052-4110&rft_id=info:doi/10.1039/d0qo00807a&rft_dat=%3Cproquest%3E2454584271%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2454584271&rft_id=info:pmid/&rfr_iscdi=true |