Chemoselective Carbozincation of Cyclopropene for C-C Bond Formation and Cleavage in a Single Operation
The carbozincation of cyclopropene and cleavage of cyclopropylzinc generates carbanion intermediates, which in turn can generate oligomeric complexes in situ through successive carbozincation reactions. The present reaction controls the carbozincation sequence and C–C bond cleavage to give densely f...
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| Veröffentlicht in: | European journal of organic chemistry 2013-10, Vol.2013 (29), p.6514-6518 |
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| container_end_page | 6518 |
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| container_issue | 29 |
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| container_title | European journal of organic chemistry |
| container_volume | 2013 |
| creator | Endo, Kohei Nakano, Takeo Fujinami, Shuhei Ukaji, Yutaka |
| description | The carbozincation of cyclopropene and cleavage of cyclopropylzinc generates carbanion intermediates, which in turn can generate oligomeric complexes in situ through successive carbozincation reactions. The present reaction controls the carbozincation sequence and C–C bond cleavage to give densely functionalized and sterically congested alkylamines in a single operation. A subtle difference in the substituent at the C=N bond induced chemoselective carbozincation of cyclopropene.
The tandem carbozincation of cyclopropene, C–C bond cleavage of the cyclopropylzinc intermediate, and allylation of an unactivated hydrazone proceeds in a single operation. The reaction gives sterically congested amines diastereoselectively. |
| doi_str_mv | 10.1002/ejoc.201301026 |
| format | Article |
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The tandem carbozincation of cyclopropene, C–C bond cleavage of the cyclopropylzinc intermediate, and allylation of an unactivated hydrazone proceeds in a single operation. The reaction gives sterically congested amines diastereoselectively.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201301026</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Allylation ; C-C activation ; Carbanions ; Domino reactions ; Zinc</subject><ispartof>European journal of organic chemistry, 2013-10, Vol.2013 (29), p.6514-6518</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4216-7eaa65c26cfc695c8f5fb0bf56fb1174fb30ea16818d4f3aad7b8a3ae55cf67b3</citedby><cites>FETCH-LOGICAL-c4216-7eaa65c26cfc695c8f5fb0bf56fb1174fb30ea16818d4f3aad7b8a3ae55cf67b3</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%2Fejoc.201301026$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201301026$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Endo, Kohei</creatorcontrib><creatorcontrib>Nakano, Takeo</creatorcontrib><creatorcontrib>Fujinami, Shuhei</creatorcontrib><creatorcontrib>Ukaji, Yutaka</creatorcontrib><title>Chemoselective Carbozincation of Cyclopropene for C-C Bond Formation and Cleavage in a Single Operation</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The carbozincation of cyclopropene and cleavage of cyclopropylzinc generates carbanion intermediates, which in turn can generate oligomeric complexes in situ through successive carbozincation reactions. The present reaction controls the carbozincation sequence and C–C bond cleavage to give densely functionalized and sterically congested alkylamines in a single operation. A subtle difference in the substituent at the C=N bond induced chemoselective carbozincation of cyclopropene.
The tandem carbozincation of cyclopropene, C–C bond cleavage of the cyclopropylzinc intermediate, and allylation of an unactivated hydrazone proceeds in a single operation. The reaction gives sterically congested amines diastereoselectively.</description><subject>Allylation</subject><subject>C-C activation</subject><subject>Carbanions</subject><subject>Domino reactions</subject><subject>Zinc</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkMtPwzAMhysEEuNx5RyJc4fTpGl7hGgbj8EmAYNblGbO6OiakY7H-OspFE3cONmWvs-2fkFwRKFLAaITnDvTjYAyoBCJraBDIctCEBlsNz1nPKQZe9wN9up6DgCZELQTzOQTLlyNJZpV8YZEap-7z6IyelW4ijhL5NqUbundEisk1nkiQ0nOXDUlfecXLaabSZao3_QMSdHM5LaoZiWS0RL9D3IQ7Fhd1nj4W_eD-37vTp6Hw9HgQp4OQ8MjKsIEtRaxiYSxRmSxSW1sc8htLGxOacJtzgA1FSlNp9wyradJnmqmMY6NFUnO9oPjdm_z8csr1is1d6--ak4qyjmLIU04NFS3pYx3de3RqqUvFtqvFQX1Hab6DlNtwmyErBXeixLX_9CqdzmSf92wdYt6hR8bV_tnJRKWxOrhZqCGYnI1noyvFWdfefqJEQ</recordid><startdate>201310</startdate><enddate>201310</enddate><creator>Endo, Kohei</creator><creator>Nakano, Takeo</creator><creator>Fujinami, Shuhei</creator><creator>Ukaji, Yutaka</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201310</creationdate><title>Chemoselective Carbozincation of Cyclopropene for C-C Bond Formation and Cleavage in a Single Operation</title><author>Endo, Kohei ; Nakano, Takeo ; Fujinami, Shuhei ; Ukaji, Yutaka</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4216-7eaa65c26cfc695c8f5fb0bf56fb1174fb30ea16818d4f3aad7b8a3ae55cf67b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Allylation</topic><topic>C-C activation</topic><topic>Carbanions</topic><topic>Domino reactions</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Endo, Kohei</creatorcontrib><creatorcontrib>Nakano, Takeo</creatorcontrib><creatorcontrib>Fujinami, Shuhei</creatorcontrib><creatorcontrib>Ukaji, Yutaka</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Endo, Kohei</au><au>Nakano, Takeo</au><au>Fujinami, Shuhei</au><au>Ukaji, Yutaka</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemoselective Carbozincation of Cyclopropene for C-C Bond Formation and Cleavage in a Single Operation</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2013-10</date><risdate>2013</risdate><volume>2013</volume><issue>29</issue><spage>6514</spage><epage>6518</epage><pages>6514-6518</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The carbozincation of cyclopropene and cleavage of cyclopropylzinc generates carbanion intermediates, which in turn can generate oligomeric complexes in situ through successive carbozincation reactions. The present reaction controls the carbozincation sequence and C–C bond cleavage to give densely functionalized and sterically congested alkylamines in a single operation. A subtle difference in the substituent at the C=N bond induced chemoselective carbozincation of cyclopropene.
The tandem carbozincation of cyclopropene, C–C bond cleavage of the cyclopropylzinc intermediate, and allylation of an unactivated hydrazone proceeds in a single operation. The reaction gives sterically congested amines diastereoselectively.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201301026</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| subjects | Allylation C-C activation Carbanions Domino reactions Zinc |
| title | Chemoselective Carbozincation of Cyclopropene for C-C Bond Formation and Cleavage in a Single Operation |
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