Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones
Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved by a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enables the cyclic enon...
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| Veröffentlicht in: | Applied organometallic chemistry 2010-07, Vol.24 (7), p.517-522 |
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| container_title | Applied organometallic chemistry |
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| creator | Gou, Shaohua Ye, Zhongbin Shi, Leiting Qing, Dayong Zhang, Wen Wang, Yuliang |
| description | Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved by a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enables the cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions. Copyright © 2010 John Wiley & Sons, Ltd.
Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved using a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enabled cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions. |
| doi_str_mv | 10.1002/aoc.1651 |
| format | Article |
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Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved using a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enabled cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions.</description><identifier>ISSN: 0268-2605</identifier><identifier>ISSN: 1099-0739</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.1651</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>addition reaction ; Asymmetry ; Catalysts ; conjugation ; copper ; enones ; Metalorganic compounds ; zinc</subject><ispartof>Applied organometallic chemistry, 2010-07, Vol.24 (7), p.517-522</ispartof><rights>Copyright © 2010 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4011-410499e97a338e6f45a39f605f37469aacbbf7447aac63d1867dbf066968e3843</citedby><cites>FETCH-LOGICAL-c4011-410499e97a338e6f45a39f605f37469aacbbf7447aac63d1867dbf066968e3843</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%2Faoc.1651$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.1651$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Gou, Shaohua</creatorcontrib><creatorcontrib>Ye, Zhongbin</creatorcontrib><creatorcontrib>Shi, Leiting</creatorcontrib><creatorcontrib>Qing, Dayong</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><creatorcontrib>Wang, Yuliang</creatorcontrib><title>Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones</title><title>Applied organometallic chemistry</title><addtitle>Appl. Organometal. Chem</addtitle><description>Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved by a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enables the cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions. Copyright © 2010 John Wiley & Sons, Ltd.
Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved using a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enabled cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions.</description><subject>addition reaction</subject><subject>Asymmetry</subject><subject>Catalysts</subject><subject>conjugation</subject><subject>copper</subject><subject>enones</subject><subject>Metalorganic compounds</subject><subject>zinc</subject><issn>0268-2605</issn><issn>1099-0739</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp10LtOwzAUBmALgUQpSDxCNhhwsWPHjscqgnKp6MJltFzHRm6TONipIH16UhUhMTCdM3z6dc4PwDlGE4xQeq28nmCW4QMwwkgIiDgRh2CEUpbDlKHsGJzEuEIICYbpCDwWvm1NgFp1quq3pkxU7OvadMHpBF9RqH2z2ryrziSqLF3nfJN4m5ROVeu-2rpGJ51PTOMbE0_BkVVVNGc_cwxebm-eizs4X8zui-kcaoowhhQjKoQRXBGSG2Zppoiww2mWcMqEUnq5tJxSPmyMlDhnvFxaxJhguSE5JWNwsc9tg__YmNjJ2kVtqko1xm-izIfXeJbhnbzcSx18jMFY2QZXq9BLjOSuLjnUJXd1DRTu6aerTP-vk9NF8de72JmvX6_CWjJOeCbfnmbyNS04Iw9MYvINM9N5ig</recordid><startdate>201007</startdate><enddate>201007</enddate><creator>Gou, Shaohua</creator><creator>Ye, Zhongbin</creator><creator>Shi, Leiting</creator><creator>Qing, Dayong</creator><creator>Zhang, Wen</creator><creator>Wang, Yuliang</creator><general>John Wiley & Sons, Ltd</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>201007</creationdate><title>Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones</title><author>Gou, Shaohua ; Ye, Zhongbin ; Shi, Leiting ; Qing, Dayong ; Zhang, Wen ; Wang, Yuliang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4011-410499e97a338e6f45a39f605f37469aacbbf7447aac63d1867dbf066968e3843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>addition reaction</topic><topic>Asymmetry</topic><topic>Catalysts</topic><topic>conjugation</topic><topic>copper</topic><topic>enones</topic><topic>Metalorganic compounds</topic><topic>zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gou, Shaohua</creatorcontrib><creatorcontrib>Ye, Zhongbin</creatorcontrib><creatorcontrib>Shi, Leiting</creatorcontrib><creatorcontrib>Qing, Dayong</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><creatorcontrib>Wang, Yuliang</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gou, Shaohua</au><au>Ye, Zhongbin</au><au>Shi, Leiting</au><au>Qing, Dayong</au><au>Zhang, Wen</au><au>Wang, Yuliang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones</atitle><jtitle>Applied organometallic chemistry</jtitle><addtitle>Appl. Organometal. Chem</addtitle><date>2010-07</date><risdate>2010</risdate><volume>24</volume><issue>7</issue><spage>517</spage><epage>522</epage><pages>517-522</pages><issn>0268-2605</issn><issn>1099-0739</issn><eissn>1099-0739</eissn><abstract>Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved by a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enables the cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions. Copyright © 2010 John Wiley & Sons, Ltd.
Asymmetric 1,4‐conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved using a 25 mol% (R)‐6,6′‐Br2‐BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enabled cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to 84% ee) and isolated yield (up to 94%) under mild reaction conditions.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/aoc.1651</doi><tpages>6</tpages></addata></record> |
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| ispartof | Applied organometallic chemistry, 2010-07, Vol.24 (7), p.517-522 |
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| source | Wiley-Blackwell Journals |
| subjects | addition reaction Asymmetry Catalysts conjugation copper enones Metalorganic compounds zinc |
| title | Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones |
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