A Facile Approach to Oximes and Ethers by a Tandem NO+‐Initiated Semipinacol Rearrangement and H‐Elimination
An efficient oximation method has been developed on the basis of NO+‐initiated semipinacol rearrangement and subsequent proton elimination. The procedure enabled the rapid construction of a series of oximes and oxime ethers with spiro quaternary stereocenters from allylic silyl ethers. Additional fe...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-10, Vol.57 (40), p.13192-13196 |
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| creator | Dong, Jia‐Wei Ding, Tongmei Zhang, Shu‐Yu Chen, Zhi‐Min Tu, Yong‐Qiang |
| description | An efficient oximation method has been developed on the basis of NO+‐initiated semipinacol rearrangement and subsequent proton elimination. The procedure enabled the rapid construction of a series of oximes and oxime ethers with spiro quaternary stereocenters from allylic silyl ethers. Additional features of this reaction include wide substrate tolerance as well as the commercial availability of the safe nitrosation reagent NOBF4. The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method.
Straight to the core: An oximation method based on NO+‐initiated semipinacol rearrangement and subsequent proton elimination enabled the rapid construction of a series of spirocyclic oximes and oxime ethers with quaternary stereocenters from allylic silyl ethers (see scheme). The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method. |
| doi_str_mv | 10.1002/anie.201807861 |
| format | Article |
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Straight to the core: An oximation method based on NO+‐initiated semipinacol rearrangement and subsequent proton elimination enabled the rapid construction of a series of spirocyclic oximes and oxime ethers with quaternary stereocenters from allylic silyl ethers (see scheme). The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201807861</identifier><identifier>PMID: 30126040</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkaloids ; Ethers ; Insecticides ; Nitrosation ; oxime ethers ; Oximes ; quaternary centers ; Reagents ; semipinacol rearrangement ; spiro compounds ; Substrates</subject><ispartof>Angewandte Chemie International Edition, 2018-10, Vol.57 (40), p.13192-13196</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4101-f9257d2565e5fee5c51a8f6138822780efa68376d8f3989f349d970f62894ae73</citedby><cites>FETCH-LOGICAL-c4101-f9257d2565e5fee5c51a8f6138822780efa68376d8f3989f349d970f62894ae73</cites><orcidid>0000-0002-9784-4052 ; 0000-0001-5800-3886 ; 0000-0002-1811-4159 ; 0000-0002-6988-8955</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%2Fanie.201807861$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201807861$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30126040$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dong, Jia‐Wei</creatorcontrib><creatorcontrib>Ding, Tongmei</creatorcontrib><creatorcontrib>Zhang, Shu‐Yu</creatorcontrib><creatorcontrib>Chen, Zhi‐Min</creatorcontrib><creatorcontrib>Tu, Yong‐Qiang</creatorcontrib><title>A Facile Approach to Oximes and Ethers by a Tandem NO+‐Initiated Semipinacol Rearrangement and H‐Elimination</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>An efficient oximation method has been developed on the basis of NO+‐initiated semipinacol rearrangement and subsequent proton elimination. The procedure enabled the rapid construction of a series of oximes and oxime ethers with spiro quaternary stereocenters from allylic silyl ethers. Additional features of this reaction include wide substrate tolerance as well as the commercial availability of the safe nitrosation reagent NOBF4. The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method.
Straight to the core: An oximation method based on NO+‐initiated semipinacol rearrangement and subsequent proton elimination enabled the rapid construction of a series of spirocyclic oximes and oxime ethers with quaternary stereocenters from allylic silyl ethers (see scheme). The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method.</description><subject>Alkaloids</subject><subject>Ethers</subject><subject>Insecticides</subject><subject>Nitrosation</subject><subject>oxime ethers</subject><subject>Oximes</subject><subject>quaternary centers</subject><subject>Reagents</subject><subject>semipinacol rearrangement</subject><subject>spiro compounds</subject><subject>Substrates</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqF0U1LHDEYB_BQKtVqrx4l4EUos83L5O24yFoXxIVqzyHOPNHITGZMZmn35kfoZ-wnaexaBS89JYRf_iTPH6FDSmaUEPbFxQAzRqgmSkv6Du1RwWjFleLvy77mvFJa0F30Mef74rUm8gPa5YQySWqyh8Y5PnNN6ADPxzENrrnD04BXP0MPGbvY4sV0Bynjmw12-LocQI8vV59_P_5axjAFN0GLr6APY4iuGTr8DVxKLt5CD3H6G3Be7KILfQFTGOIB2vGuy_Dped1H388W16fn1cXq6_J0flE1NSW08oYJ1TIhBQgPIBpBnfaScq0ZU5qAd1JzJVvtudHG89q0RhEvmTa1A8X30ck2t_zqYQ15sn3IDXSdizCss2XEUMYl4aTQ4zf0flinWF5nGaVUiJpxU9Rsq5o05JzA2zGF3qWNpcQ-dWGfurAvXZQLR8-x65se2hf-b_gFmC34Uea_-U-cnV8uF6_hfwAWhZVf</recordid><startdate>20181001</startdate><enddate>20181001</enddate><creator>Dong, Jia‐Wei</creator><creator>Ding, Tongmei</creator><creator>Zhang, Shu‐Yu</creator><creator>Chen, Zhi‐Min</creator><creator>Tu, Yong‐Qiang</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9784-4052</orcidid><orcidid>https://orcid.org/0000-0001-5800-3886</orcidid><orcidid>https://orcid.org/0000-0002-1811-4159</orcidid><orcidid>https://orcid.org/0000-0002-6988-8955</orcidid></search><sort><creationdate>20181001</creationdate><title>A Facile Approach to Oximes and Ethers by a Tandem NO+‐Initiated Semipinacol Rearrangement and H‐Elimination</title><author>Dong, Jia‐Wei ; Ding, Tongmei ; Zhang, Shu‐Yu ; Chen, Zhi‐Min ; Tu, Yong‐Qiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4101-f9257d2565e5fee5c51a8f6138822780efa68376d8f3989f349d970f62894ae73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkaloids</topic><topic>Ethers</topic><topic>Insecticides</topic><topic>Nitrosation</topic><topic>oxime ethers</topic><topic>Oximes</topic><topic>quaternary centers</topic><topic>Reagents</topic><topic>semipinacol rearrangement</topic><topic>spiro compounds</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dong, Jia‐Wei</creatorcontrib><creatorcontrib>Ding, Tongmei</creatorcontrib><creatorcontrib>Zhang, Shu‐Yu</creatorcontrib><creatorcontrib>Chen, Zhi‐Min</creatorcontrib><creatorcontrib>Tu, Yong‐Qiang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dong, Jia‐Wei</au><au>Ding, Tongmei</au><au>Zhang, Shu‐Yu</au><au>Chen, Zhi‐Min</au><au>Tu, Yong‐Qiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Facile Approach to Oximes and Ethers by a Tandem NO+‐Initiated Semipinacol Rearrangement and H‐Elimination</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-10-01</date><risdate>2018</risdate><volume>57</volume><issue>40</issue><spage>13192</spage><epage>13196</epage><pages>13192-13196</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An efficient oximation method has been developed on the basis of NO+‐initiated semipinacol rearrangement and subsequent proton elimination. The procedure enabled the rapid construction of a series of oximes and oxime ethers with spiro quaternary stereocenters from allylic silyl ethers. Additional features of this reaction include wide substrate tolerance as well as the commercial availability of the safe nitrosation reagent NOBF4. The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method.
Straight to the core: An oximation method based on NO+‐initiated semipinacol rearrangement and subsequent proton elimination enabled the rapid construction of a series of spirocyclic oximes and oxime ethers with quaternary stereocenters from allylic silyl ethers (see scheme). The key N‐heterotricyclic cores of three natural alkaloids, tuberostemoninol B, (+)‐quebrachidine, and an insecticide, were also constructed efficiently by this method.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30126040</pmid><doi>10.1002/anie.201807861</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-9784-4052</orcidid><orcidid>https://orcid.org/0000-0001-5800-3886</orcidid><orcidid>https://orcid.org/0000-0002-1811-4159</orcidid><orcidid>https://orcid.org/0000-0002-6988-8955</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkaloids Ethers Insecticides Nitrosation oxime ethers Oximes quaternary centers Reagents semipinacol rearrangement spiro compounds Substrates |
| title | A Facile Approach to Oximes and Ethers by a Tandem NO+‐Initiated Semipinacol Rearrangement and H‐Elimination |
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