Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor
Anything between ureas? Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, ar...
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| Veröffentlicht in: | Chemistry : a European journal 2013-02, Vol.19 (6), p.1914-1918 |
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| container_end_page | 1918 |
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| container_issue | 6 |
| container_start_page | 1914 |
| container_title | Chemistry : a European journal |
| container_volume | 19 |
| creator | Shi, Yan Lin, Aijun Mao, Haibin Mao, Zhijie Li, Weipeng Hu, Hongwen Zhu, Chengjian Cheng, Yixiang |
| description | Anything between ureas? Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio‐ and diastereoselectivity. The bisthiourea catalyst acts as a multiple‐hydrogen‐bond donor to simultaneously activate both substrates. |
| doi_str_mv | 10.1002/chem.201202937 |
| format | Article |
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Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio‐ and diastereoselectivity. The bisthiourea catalyst acts as a multiple‐hydrogen‐bond donor to simultaneously activate both substrates.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201202937</identifier><identifier>PMID: 23281117</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>asymmetric synthesis ; bisthioureas ; Catalysis ; Catalysts ; Chemical reactions ; Chemistry ; Construction ; Construction materials ; Cyclization ; Derivatives ; Hydrogen Bonding ; hydrogen bonds ; Indoles - chemical synthesis ; Indoles - chemistry ; Molecular Structure ; Organic chemistry ; spiro compounds ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; Stereoisomerism ; synthetic methods ; Thiourea - chemistry ; Ureas</subject><ispartof>Chemistry : a European journal, 2013-02, Vol.19 (6), p.1914-1918</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><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-c5387-55e8af19669dadd93edf5769dd418265642cabb8a3d14670e9708026169b00203</citedby><cites>FETCH-LOGICAL-c5387-55e8af19669dadd93edf5769dd418265642cabb8a3d14670e9708026169b00203</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%2Fchem.201202937$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201202937$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23281117$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shi, Yan</creatorcontrib><creatorcontrib>Lin, Aijun</creatorcontrib><creatorcontrib>Mao, Haibin</creatorcontrib><creatorcontrib>Mao, Zhijie</creatorcontrib><creatorcontrib>Li, Weipeng</creatorcontrib><creatorcontrib>Hu, Hongwen</creatorcontrib><creatorcontrib>Zhu, Chengjian</creatorcontrib><creatorcontrib>Cheng, Yixiang</creatorcontrib><title>Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Anything between ureas? Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio‐ and diastereoselectivity. The bisthiourea catalyst acts as a multiple‐hydrogen‐bond donor to simultaneously activate both substrates.</description><subject>asymmetric synthesis</subject><subject>bisthioureas</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Construction</subject><subject>Construction materials</subject><subject>Cyclization</subject><subject>Derivatives</subject><subject>Hydrogen Bonding</subject><subject>hydrogen bonds</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>spiro compounds</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>Stereoisomerism</subject><subject>synthetic methods</subject><subject>Thiourea - chemistry</subject><subject>Ureas</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1uEzEUhUcIREthyxJZYoOEJvhnbI-XbRISRFqE-FsgZDnjm8btxA72TGl4Ch4Zh5QIscnKutZ3jnX9FcVTggcEY_qqWcJqQDGhmCom7xXHhFNSMin4_eIYq0qWgjN1VDxK6QpjrARjD4sjymhNCJHHxa-xN75zIUELTeduAA2DT13s8xA8Cgv0Ye1iCLfO29ACGkF0N2YLJtQtY-gvl-gre0m_oVPv-9b8SQ1NZ9rNT7BovkEGnbnULV3oIxhkUr4479vOrVsopxsbwyX48ix4i0bBh_i4eLAwbYInd-dJ8en1-ONwWs7eTd4MT2dlw1ktS86hNguihFDWWKsY2AWXebAVqangoqKNmc9rwyyphMSgJK4xFUSoef43zE6KF7vedQzfe0idXrnUQNsaD6FPmkhZ4ypH2GGU1rRmFZNVRp__h17lvX1eZEtVhAhe0wMUpVwRvH12sKOaGFKKsNDr6FYmbjTBeitfb-XrvfwceHZX289XYPf4X9sZUDvgh2thc6BOD6fj83_Ly102y4TbfdbEay0kk1x_uZjo0cXbyfvZZ6Y5-w10VcnM</recordid><startdate>20130204</startdate><enddate>20130204</enddate><creator>Shi, Yan</creator><creator>Lin, Aijun</creator><creator>Mao, Haibin</creator><creator>Mao, Zhijie</creator><creator>Li, Weipeng</creator><creator>Hu, Hongwen</creator><creator>Zhu, Chengjian</creator><creator>Cheng, Yixiang</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20130204</creationdate><title>Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor</title><author>Shi, Yan ; Lin, Aijun ; Mao, Haibin ; Mao, Zhijie ; Li, Weipeng ; Hu, Hongwen ; Zhu, Chengjian ; Cheng, Yixiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5387-55e8af19669dadd93edf5769dd418265642cabb8a3d14670e9708026169b00203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>asymmetric synthesis</topic><topic>bisthioureas</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Construction</topic><topic>Construction materials</topic><topic>Cyclization</topic><topic>Derivatives</topic><topic>Hydrogen Bonding</topic><topic>hydrogen bonds</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>spiro compounds</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - chemistry</topic><topic>Stereoisomerism</topic><topic>synthetic methods</topic><topic>Thiourea - chemistry</topic><topic>Ureas</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shi, Yan</creatorcontrib><creatorcontrib>Lin, Aijun</creatorcontrib><creatorcontrib>Mao, Haibin</creatorcontrib><creatorcontrib>Mao, Zhijie</creatorcontrib><creatorcontrib>Li, Weipeng</creatorcontrib><creatorcontrib>Hu, Hongwen</creatorcontrib><creatorcontrib>Zhu, Chengjian</creatorcontrib><creatorcontrib>Cheng, Yixiang</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shi, Yan</au><au>Lin, Aijun</au><au>Mao, Haibin</au><au>Mao, Zhijie</au><au>Li, Weipeng</au><au>Hu, Hongwen</au><au>Zhu, Chengjian</au><au>Cheng, Yixiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2013-02-04</date><risdate>2013</risdate><volume>19</volume><issue>6</issue><spage>1914</spage><epage>1918</epage><pages>1914-1918</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Anything between ureas? Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio‐ and diastereoselectivity. The bisthiourea catalyst acts as a multiple‐hydrogen‐bond donor to simultaneously activate both substrates.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23281117</pmid><doi>10.1002/chem.201202937</doi><tpages>5</tpages></addata></record> |
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| source | MEDLINE; Access via Wiley Online Library |
| subjects | asymmetric synthesis bisthioureas Catalysis Catalysts Chemical reactions Chemistry Construction Construction materials Cyclization Derivatives Hydrogen Bonding hydrogen bonds Indoles - chemical synthesis Indoles - chemistry Molecular Structure Organic chemistry spiro compounds Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism synthetic methods Thiourea - chemistry Ureas |
| title | Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor |
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