Rapid Access to Oxabicyclo[2.2.2]octane Skeleton through Cu(I)‐Catalyzed Generation and Trapping of Vinyl‐o‐quinodimethanes (Vinyl‐o‐QDMs)
A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed thro...
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| Veröffentlicht in: | Chinese journal of chemistry 2020-10, Vol.38 (10), p.1052-1056 |
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| container_title | Chinese journal of chemistry |
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| creator | Luo, Hejiang He, Chuan Jiang, Huanfeng Zhu, Shifa |
| description | A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes.
Summary of main observation and conclusion
A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes. The obvious advantages of wide substrate scopes, mild reaction conditions, and high seteroselectivity and atom efficiency make this reaction highly appealing for construction of highly rigid [2.2.2]octane skeleton. |
| doi_str_mv | 10.1002/cjoc.202000144 |
| format | Article |
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Summary of main observation and conclusion
A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes. The obvious advantages of wide substrate scopes, mild reaction conditions, and high seteroselectivity and atom efficiency make this reaction highly appealing for construction of highly rigid [2.2.2]octane skeleton.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.202000144</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Carbene ; Copper ; Cycloaddition ; Oxabicyclo[2.2.2]octane ; o‐Quinodimethane</subject><ispartof>Chinese journal of chemistry, 2020-10, Vol.38 (10), p.1052-1056</ispartof><rights>2020 SIOC, CAS, Shanghai and Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3264-816f27177d2917bddf0d4059a22fb269403c079a7d6ef53b49fab0c8b79ccb963</citedby><cites>FETCH-LOGICAL-c3264-816f27177d2917bddf0d4059a22fb269403c079a7d6ef53b49fab0c8b79ccb963</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%2Fcjoc.202000144$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcjoc.202000144$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids></links><search><creatorcontrib>Luo, Hejiang</creatorcontrib><creatorcontrib>He, Chuan</creatorcontrib><creatorcontrib>Jiang, Huanfeng</creatorcontrib><creatorcontrib>Zhu, Shifa</creatorcontrib><title>Rapid Access to Oxabicyclo[2.2.2]octane Skeleton through Cu(I)‐Catalyzed Generation and Trapping of Vinyl‐o‐quinodimethanes (Vinyl‐o‐QDMs)</title><title>Chinese journal of chemistry</title><description>A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes.
Summary of main observation and conclusion
A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes. The obvious advantages of wide substrate scopes, mild reaction conditions, and high seteroselectivity and atom efficiency make this reaction highly appealing for construction of highly rigid [2.2.2]octane skeleton.</description><subject>Carbene</subject><subject>Copper</subject><subject>Cycloaddition</subject><subject>Oxabicyclo[2.2.2]octane</subject><subject>o‐Quinodimethane</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkL9OwzAQxiMEEqWwMntshwTbSe1mrAKUoqIKKAgJocjxn9YljUOcCsLEIzDwhDwJroqADZ1Od7r7fd_wed4hggGCEB_xheEBhhhCiKJoy2shgiKfQtLbdrs7-gRGd7venrULx1OKScv7uGKlFmDAubQW1AZMXlimecNzc48DVw-G16yQ4PpR5rI2BajnlVnN5iBZdUbdz7f3hNUsb16lAENZyIrV2kGsEGBasbLUxQwYBW510eQONq6fVrowQi9lPXfGFnT-Pi-PL2x339tRLLfy4Hu2vZvTk2ly5o8nw1EyGPs8xCTy-4goTBGlAseIZkIoKCLYixnGKsMkjmDIIY0ZFUSqXphFsWIZ5P2MxpxnMQnbXrDx5ZWxtpIqLSu9ZFWTIpiuM03XmaY_mTpBvBE861w2_9Bpcj5JfrVfkGqBfQ</recordid><startdate>202010</startdate><enddate>202010</enddate><creator>Luo, Hejiang</creator><creator>He, Chuan</creator><creator>Jiang, Huanfeng</creator><creator>Zhu, Shifa</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>202010</creationdate><title>Rapid Access to Oxabicyclo[2.2.2]octane Skeleton through Cu(I)‐Catalyzed Generation and Trapping of Vinyl‐o‐quinodimethanes (Vinyl‐o‐QDMs)</title><author>Luo, Hejiang ; He, Chuan ; Jiang, Huanfeng ; Zhu, Shifa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3264-816f27177d2917bddf0d4059a22fb269403c079a7d6ef53b49fab0c8b79ccb963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Carbene</topic><topic>Copper</topic><topic>Cycloaddition</topic><topic>Oxabicyclo[2.2.2]octane</topic><topic>o‐Quinodimethane</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Hejiang</creatorcontrib><creatorcontrib>He, Chuan</creatorcontrib><creatorcontrib>Jiang, Huanfeng</creatorcontrib><creatorcontrib>Zhu, Shifa</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Hejiang</au><au>He, Chuan</au><au>Jiang, Huanfeng</au><au>Zhu, Shifa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rapid Access to Oxabicyclo[2.2.2]octane Skeleton through Cu(I)‐Catalyzed Generation and Trapping of Vinyl‐o‐quinodimethanes (Vinyl‐o‐QDMs)</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2020-10</date><risdate>2020</risdate><volume>38</volume><issue>10</issue><spage>1052</spage><epage>1056</epage><pages>1052-1056</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes.
Summary of main observation and conclusion
A Cu(I)‐catalyzed three‐component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl‐o‐quinodimethanes (vinyl‐o‐QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes. The obvious advantages of wide substrate scopes, mild reaction conditions, and high seteroselectivity and atom efficiency make this reaction highly appealing for construction of highly rigid [2.2.2]octane skeleton.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.202000144</doi><tpages>5</tpages></addata></record> |
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| ispartof | Chinese journal of chemistry, 2020-10, Vol.38 (10), p.1052-1056 |
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| language | eng |
| recordid | cdi_crossref_primary_10_1002_cjoc_202000144 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Carbene Copper Cycloaddition Oxabicyclo[2.2.2]octane o‐Quinodimethane |
| title | Rapid Access to Oxabicyclo[2.2.2]octane Skeleton through Cu(I)‐Catalyzed Generation and Trapping of Vinyl‐o‐quinodimethanes (Vinyl‐o‐QDMs) |
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