Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System
The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantiose...
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| Veröffentlicht in: | Journal of organic chemistry 2004-11, Vol.69 (24), p.8500-8503 |
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| container_end_page | 8503 |
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| container_issue | 24 |
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| container_title | Journal of organic chemistry |
| container_volume | 69 |
| creator | Sun, Jiangtao Zhu, Chengjian Dai, Zhenya Yang, Minghua Pan, Yi Hu, Hongwen |
| description | The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium−salan system is also described. |
| doi_str_mv | 10.1021/jo040221d |
| format | Article |
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The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. 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Org. Chem</addtitle><description>The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium−salan system is also described.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Kinetics</subject><subject>Ligands</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Salicylates - chemistry</subject><subject>Solution properties</subject><subject>Solutions</subject><subject>Sulfides - chemistry</subject><subject>Sulfoxides - chemical synthesis</subject><subject>Sulfoxides - chemistry</subject><subject>Vanadium - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0ctuEzEUBmALgWgILHgB5A1IXQwc22NnvKyiUi6VipLSrXXGY0sucyn2DMrwBKx5RJ4EQ6KGBd5Y8vl09Os3Ic8ZvGbA2ZvbAUrgnDUPyIJJDoXSUD4kC8iPheBKnJAnKd1CPlLKx-SESVnqiusF-XbufbDB9SM9S3PXuTEGS692ocExDD0dPN1OrQ-NSxT7hn4MvRuz2Lg0tNO_ZNj9RWscsZ2_u4bWM0V6gz02Yep-_fi5xRZ7up3T6Lqn5JHHNrlnh3tJPr89v16_Ky6vLt6vzy4LLEs5FraSCoS3CmpXOw2VLbXUSgpW1VI4awE91LJSvNZSrpxAaevMlNS8BOHEkrza772Lw9fJpdF0IVnX5iRumJJRK9DA2CrD0z20cUgpOm_uYugwzoaB-VOyuS852xeHpVPdueYoD61m8PIAMFlsfcTehnR0SkDF87csSbF3IXeyu59j_JKDiZU015-2ZrMuK3Wz-WDYcS_alPNMsc_d_SfgbxPXoJM</recordid><startdate>20041126</startdate><enddate>20041126</enddate><creator>Sun, Jiangtao</creator><creator>Zhu, Chengjian</creator><creator>Dai, Zhenya</creator><creator>Yang, Minghua</creator><creator>Pan, Yi</creator><creator>Hu, Hongwen</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20041126</creationdate><title>Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System</title><author>Sun, Jiangtao ; Zhu, Chengjian ; Dai, Zhenya ; Yang, Minghua ; Pan, Yi ; Hu, Hongwen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-c85603fc60bebe908c495965318b53ecc0af0b5862b9557e3a5cb9086592403e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Kinetics</topic><topic>Ligands</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Salicylates - chemistry</topic><topic>Solution properties</topic><topic>Solutions</topic><topic>Sulfides - chemistry</topic><topic>Sulfoxides - chemical synthesis</topic><topic>Sulfoxides - chemistry</topic><topic>Vanadium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Jiangtao</creatorcontrib><creatorcontrib>Zhu, Chengjian</creatorcontrib><creatorcontrib>Dai, Zhenya</creatorcontrib><creatorcontrib>Yang, Minghua</creatorcontrib><creatorcontrib>Pan, Yi</creatorcontrib><creatorcontrib>Hu, Hongwen</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Jiangtao</au><au>Zhu, Chengjian</au><au>Dai, Zhenya</au><au>Yang, Minghua</au><au>Pan, Yi</au><au>Hu, Hongwen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-11-26</date><risdate>2004</risdate><volume>69</volume><issue>24</issue><spage>8500</spage><epage>8503</epage><pages>8500-8503</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium−salan system is also described.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15549829</pmid><doi>10.1021/jo040221d</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2004-11, Vol.69 (24), p.8500-8503 |
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| language | eng |
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| subjects | Catalysis Chemistry Exact sciences and technology General and physical chemistry Kinetics Ligands Molecular Structure Organometallic Compounds - chemistry Oxidation-Reduction Salicylates - chemistry Solution properties Solutions Sulfides - chemistry Sulfoxides - chemical synthesis Sulfoxides - chemistry Vanadium - chemistry |
| title | Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System |
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