A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers
The immobilization of dirhodium(II) tetrakis[N‐tetrafluorophthaloyl‐(S)‐tert‐leucinate], [Rh2(S‐TFPTTL)4], has been accomplished by copolymerization of a dirhodium(II) complex‐containing monomer with styrene and 1,6‐bis(4‐vinylbenzyloxy)hexane as a flexible cross‐linker. The polymer‐supported chiral...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2012-08, Vol.354 (11-12), p.2331-2338 |
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| container_issue | 11-12 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Oohara, Tadashi Nambu, Hisanori Anada, Masahiro Takeda, Koji Hashimoto, Shunichi |
| description | The immobilization of dirhodium(II) tetrakis[N‐tetrafluorophthaloyl‐(S)‐tert‐leucinate], [Rh2(S‐TFPTTL)4], has been accomplished by copolymerization of a dirhodium(II) complex‐containing monomer with styrene and 1,6‐bis(4‐vinylbenzyloxy)hexane as a flexible cross‐linker. The polymer‐supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N‐(2‐nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh) to provide α‐amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant. |
| doi_str_mv | 10.1002/adsc.201200219 |
| format | Article |
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The polymer‐supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N‐(2‐nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh) to provide α‐amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201200219</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Applied sciences ; asymmetric catalysis ; Catalysis ; Catalysts: preparations and properties ; Catalytic reactions ; Chemistry ; Copolymerization ; Exact sciences and technology ; General and physical chemistry ; heterogeneous catalysis ; immobilization ; nitrenes ; Noncondensed benzenic compounds ; Organic chemistry ; Organic polymers ; Physicochemistry of polymers ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; Preparations and properties ; rhodium ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Advanced synthesis & catalysis, 2012-08, Vol.354 (11-12), p.2331-2338</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4239-5e0334172ff623dd53d359575e6c873effe2e9fef6167218a4b8a0fd446a4e93</citedby><cites>FETCH-LOGICAL-c4239-5e0334172ff623dd53d359575e6c873effe2e9fef6167218a4b8a0fd446a4e93</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%2Fadsc.201200219$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201200219$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26346137$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Oohara, Tadashi</creatorcontrib><creatorcontrib>Nambu, Hisanori</creatorcontrib><creatorcontrib>Anada, Masahiro</creatorcontrib><creatorcontrib>Takeda, Koji</creatorcontrib><creatorcontrib>Hashimoto, Shunichi</creatorcontrib><title>A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>The immobilization of dirhodium(II) tetrakis[N‐tetrafluorophthaloyl‐(S)‐tert‐leucinate], [Rh2(S‐TFPTTL)4], has been accomplished by copolymerization of a dirhodium(II) complex‐containing monomer with styrene and 1,6‐bis(4‐vinylbenzyloxy)hexane as a flexible cross‐linker. The polymer‐supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N‐(2‐nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh) to provide α‐amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.</description><subject>Applied sciences</subject><subject>asymmetric catalysis</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Catalytic reactions</subject><subject>Chemistry</subject><subject>Copolymerization</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>heterogeneous catalysis</subject><subject>immobilization</subject><subject>nitrenes</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Preparations and properties</subject><subject>rhodium</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkEtLAzEUhQdRsFa3rrMRdDE173SWw_RhpWixRZchziQ0NdMMSYudf29Lpbhzc1-c71w4SXKLYA9BiB9VFcsehgjvF5SdJR3EEUsp4tn5aWbwMrmKcQUhEn0hOskqBzPv2lqHdL5tGh82ugLF0gblwMhtfbBrdTgNbFj6ym7r-8nkARS-bpzeAeMDyGNb13oTbAny-qC2fg28AXPrWgeGa78vm6UO8Tq5MMpFffPbu8liNFwUT-n0dTwp8mlaUkyylGlICEUCG8MxqSpGKsIyJpjmZV8QbYzGOjPacMQFRn1FP_sKmopSrqjOSDfpHW3L4GMM2sgm2FqFViIoD0HJQ1DyFNQeuDsCjYqlciaodWnjicKcUI6I2Ouyo-7bOt3-4yrzwbz4-yM9sjZu9O7EqvAluSCCyY-XsUSMwGc6e5dv5Ad53okW</recordid><startdate>20120813</startdate><enddate>20120813</enddate><creator>Oohara, Tadashi</creator><creator>Nambu, Hisanori</creator><creator>Anada, Masahiro</creator><creator>Takeda, Koji</creator><creator>Hashimoto, Shunichi</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20120813</creationdate><title>A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers</title><author>Oohara, Tadashi ; Nambu, Hisanori ; Anada, Masahiro ; Takeda, Koji ; Hashimoto, Shunichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4239-5e0334172ff623dd53d359575e6c873effe2e9fef6167218a4b8a0fd446a4e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Applied sciences</topic><topic>asymmetric catalysis</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Catalytic reactions</topic><topic>Chemistry</topic><topic>Copolymerization</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>heterogeneous catalysis</topic><topic>immobilization</topic><topic>nitrenes</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Preparations and properties</topic><topic>rhodium</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oohara, Tadashi</creatorcontrib><creatorcontrib>Nambu, Hisanori</creatorcontrib><creatorcontrib>Anada, Masahiro</creatorcontrib><creatorcontrib>Takeda, Koji</creatorcontrib><creatorcontrib>Hashimoto, Shunichi</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oohara, Tadashi</au><au>Nambu, Hisanori</au><au>Anada, Masahiro</au><au>Takeda, Koji</au><au>Hashimoto, Shunichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2012-08-13</date><risdate>2012</risdate><volume>354</volume><issue>11-12</issue><spage>2331</spage><epage>2338</epage><pages>2331-2338</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The immobilization of dirhodium(II) tetrakis[N‐tetrafluorophthaloyl‐(S)‐tert‐leucinate], [Rh2(S‐TFPTTL)4], has been accomplished by copolymerization of a dirhodium(II) complex‐containing monomer with styrene and 1,6‐bis(4‐vinylbenzyloxy)hexane as a flexible cross‐linker. The polymer‐supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N‐(2‐nitrophenylsulfonyl)imino]phenyliodinane (NsNIPh) to provide α‐amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201200219</doi><tpages>8</tpages></addata></record> |
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| subjects | Applied sciences asymmetric catalysis Catalysis Catalysts: preparations and properties Catalytic reactions Chemistry Copolymerization Exact sciences and technology General and physical chemistry heterogeneous catalysis immobilization nitrenes Noncondensed benzenic compounds Organic chemistry Organic polymers Physicochemistry of polymers Preparation, kinetics, thermodynamics, mechanism and catalysts Preparations and properties rhodium Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers |
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