Transition‐Metal‐Free Synthesis of Electron Rich 1,3‐Dienes via Base Promoted Isomerization of Propargylic Ethers
Herein, a novel and scalable synthesis of electron rich 1,3‐dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could b...
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| Veröffentlicht in: | European journal of organic chemistry 2020-01, Vol.2020 (4), p.483-487 |
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| container_end_page | 487 |
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| container_issue | 4 |
| container_start_page | 483 |
| container_title | European journal of organic chemistry |
| container_volume | 2020 |
| creator | Liu, Chunxiang Deng, Guogang Li, Xin Xu, Yiren Yu, Kaili Chen, Wen Zhang, Hongbin Yang, Xiaodong |
| description | Herein, a novel and scalable synthesis of electron rich 1,3‐dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.
An efficient and broadly applicable method for the construction of functionalized electron rich 1,3‐dienes through a base promoted isomerization reaction of propargylic ethers is presented. This process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for late stage modification of natural products. |
| doi_str_mv | 10.1002/ejoc.201901743 |
| format | Article |
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An efficient and broadly applicable method for the construction of functionalized electron rich 1,3‐dienes through a base promoted isomerization reaction of propargylic ethers is presented. This process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for late stage modification of natural products.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201901743</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Diels‐Alder reactions ; Dienes ; Ethers ; Isomerization ; Natural products ; Propargylic ethers ; Synthesis ; Transition‐metal‐free synthesis</subject><ispartof>European journal of organic chemistry, 2020-01, Vol.2020 (4), p.483-487</ispartof><rights>2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-153d84389d789fc1128f15de52ecb9c22675d79a47f565c868670c7a95c590143</citedby><cites>FETCH-LOGICAL-c3173-153d84389d789fc1128f15de52ecb9c22675d79a47f565c868670c7a95c590143</cites><orcidid>0000-0002-8466-5418 ; 0000-0002-2516-2634</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201901743$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201901743$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Liu, Chunxiang</creatorcontrib><creatorcontrib>Deng, Guogang</creatorcontrib><creatorcontrib>Li, Xin</creatorcontrib><creatorcontrib>Xu, Yiren</creatorcontrib><creatorcontrib>Yu, Kaili</creatorcontrib><creatorcontrib>Chen, Wen</creatorcontrib><creatorcontrib>Zhang, Hongbin</creatorcontrib><creatorcontrib>Yang, Xiaodong</creatorcontrib><title>Transition‐Metal‐Free Synthesis of Electron Rich 1,3‐Dienes via Base Promoted Isomerization of Propargylic Ethers</title><title>European journal of organic chemistry</title><description>Herein, a novel and scalable synthesis of electron rich 1,3‐dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.
An efficient and broadly applicable method for the construction of functionalized electron rich 1,3‐dienes through a base promoted isomerization reaction of propargylic ethers is presented. This process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for late stage modification of natural products.</description><subject>Diels‐Alder reactions</subject><subject>Dienes</subject><subject>Ethers</subject><subject>Isomerization</subject><subject>Natural products</subject><subject>Propargylic ethers</subject><subject>Synthesis</subject><subject>Transition‐metal‐free synthesis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQhiMEEqWwMltiJcWO4yQeoaRQVFQERWKzjHOhrtK42ClVmHgEnpEnwVERjEx30n3_f9IXBMcEDwjG0RksjBpEmHBM0pjuBD2COQ9xwvGu32Mah4TTp_3gwLkFxpgnCekFm5mVtdONNvXXx-ctNLLyc2QB0ENbN3Nw2iFTorwC1VhTo3ut5oicUk9daqjBoTct0YV0gO6sWZoGCjR2ZglWv8uutkv7y0ral7bSCuW-1LrDYK-UlYOjn9kPHkf5bHgdTqZX4-H5JFSUpDQkjBZZTDNepBkvFSFRVhJWAItAPXMVRUnKipTLOC1ZwlSWZEmKVSo5U8x7iGk_ONn2rqx5XYNrxMKsbe1fiojGjHWOMk8NtpSyxjkLpVhZvZS2FQSLTq7o5IpfuT7At4GNrqD9hxb5zXT4l_0GwrKAxg</recordid><startdate>20200131</startdate><enddate>20200131</enddate><creator>Liu, Chunxiang</creator><creator>Deng, Guogang</creator><creator>Li, Xin</creator><creator>Xu, Yiren</creator><creator>Yu, Kaili</creator><creator>Chen, Wen</creator><creator>Zhang, Hongbin</creator><creator>Yang, Xiaodong</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-8466-5418</orcidid><orcidid>https://orcid.org/0000-0002-2516-2634</orcidid></search><sort><creationdate>20200131</creationdate><title>Transition‐Metal‐Free Synthesis of Electron Rich 1,3‐Dienes via Base Promoted Isomerization of Propargylic Ethers</title><author>Liu, Chunxiang ; Deng, Guogang ; Li, Xin ; Xu, Yiren ; Yu, Kaili ; Chen, Wen ; Zhang, Hongbin ; Yang, Xiaodong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-153d84389d789fc1128f15de52ecb9c22675d79a47f565c868670c7a95c590143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Diels‐Alder reactions</topic><topic>Dienes</topic><topic>Ethers</topic><topic>Isomerization</topic><topic>Natural products</topic><topic>Propargylic ethers</topic><topic>Synthesis</topic><topic>Transition‐metal‐free synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Chunxiang</creatorcontrib><creatorcontrib>Deng, Guogang</creatorcontrib><creatorcontrib>Li, Xin</creatorcontrib><creatorcontrib>Xu, Yiren</creatorcontrib><creatorcontrib>Yu, Kaili</creatorcontrib><creatorcontrib>Chen, Wen</creatorcontrib><creatorcontrib>Zhang, Hongbin</creatorcontrib><creatorcontrib>Yang, Xiaodong</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Chunxiang</au><au>Deng, Guogang</au><au>Li, Xin</au><au>Xu, Yiren</au><au>Yu, Kaili</au><au>Chen, Wen</au><au>Zhang, Hongbin</au><au>Yang, Xiaodong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition‐Metal‐Free Synthesis of Electron Rich 1,3‐Dienes via Base Promoted Isomerization of Propargylic Ethers</atitle><jtitle>European journal of organic chemistry</jtitle><date>2020-01-31</date><risdate>2020</risdate><volume>2020</volume><issue>4</issue><spage>483</spage><epage>487</epage><pages>483-487</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Herein, a novel and scalable synthesis of electron rich 1,3‐dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.
An efficient and broadly applicable method for the construction of functionalized electron rich 1,3‐dienes through a base promoted isomerization reaction of propargylic ethers is presented. This process features easy handling reaction conditions, transition‐metal‐free isomerization, high isolated yields, and most of all, it could be used for late stage modification of natural products.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201901743</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-8466-5418</orcidid><orcidid>https://orcid.org/0000-0002-2516-2634</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2020-01, Vol.2020 (4), p.483-487 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Diels‐Alder reactions Dienes Ethers Isomerization Natural products Propargylic ethers Synthesis Transition‐metal‐free synthesis |
| title | Transition‐Metal‐Free Synthesis of Electron Rich 1,3‐Dienes via Base Promoted Isomerization of Propargylic Ethers |
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