Computational Study-Led Organocatalyst Design: A Novel, Highly Active Urea-Based Catalyst for Addition Reactions to Epoxides
An in silico study examined the stabilities of hydrogen-bonded complexes between simple thiourea catalysts and three different electrophiles and identified a novel, highly active N-tosyl urea catalyst for the promotion of addition reactions to epoxide electrophiles. Synthesis and evaluation of 6 rev...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2008-02, Vol.73 (3), p.948-956 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 956 |
|---|---|
| container_issue | 3 |
| container_start_page | 948 |
| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | Fleming, Eimear M Quigley, Cormac Rozas, Isabel Connon, Stephen J |
| description | An in silico study examined the stabilities of hydrogen-bonded complexes between simple thiourea catalysts and three different electrophiles and identified a novel, highly active N-tosyl urea catalyst for the promotion of addition reactions to epoxide electrophiles. Synthesis and evaluation of 6 revealed it to be a powerful catalyst for the addition of 1,2-dimethylindole to styrene oxide under conditions in which simple N,N-bis-aryl ureas and thioureas (including 1) are inactive. Subsequent studies determined 6 to be compatible with a range of indole and epoxide substrates (including (E)-stilbene oxide) and found that relatively poor nucleophiles such as sterically and electronically deactivated anilines, thiophenol, and benzyl alcohol could be efficiently and regioselectively added to oxiranes under mild conditions. |
| doi_str_mv | 10.1021/jo702154m |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_70237577</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>70237577</sourcerecordid><originalsourceid>FETCH-LOGICAL-a447t-8e6b8b7efcab5900f62396233ee7537a603bdfae6ed0561c8eff30d26f05e07c3</originalsourceid><addsrcrecordid>eNptkc9uEzEQxi0EomnhwAsgX0BCYsG7Xq-T3kLaUlBEUf9ccrFmvePgsrsOtrdqTnDlNXkSHCWkF0ayZiT_5tOnbwh5kbN3OSvy97dOpibK7hEZ5aJgWTVh5WMyYqwoMl5U_IAchnDLUgkhnpKDfJxLXoyrEfk5c91qiBCt66GlV3Fo1tkcG3rhl9A7DRHadYj0BINd9sd_fv2mU_rF3WH7lp7b5bd2Tac62jukNx4h-wAh7c7-bRnn6bRp7EadXiLozRBodPR05e5tg-EZeWKgDfh814_Izdnp9ew8m198_DSbzjMoSxmzMVb1uJZoNNRiwpipCj5JjyNKwSVUjNeNAaywYaLK9RiN4awpKsMEMqn5EXm91V1592PAEFVng8a2hR7dEFQKkEshZQLfbEHtXQgejVp524Ffq5ypTdpqn3ZiX-5Eh7rD5oHcxZuAVzsAgobWeOi1DXuuYKyUgpWJy7acDRHv9__gv6tKJl_q-uuV4peL8ixffFaLB13QIfkZfLpd-I_Bv5DGpEs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>70237577</pqid></control><display><type>article</type><title>Computational Study-Led Organocatalyst Design: A Novel, Highly Active Urea-Based Catalyst for Addition Reactions to Epoxides</title><source>ACS Publications</source><creator>Fleming, Eimear M ; Quigley, Cormac ; Rozas, Isabel ; Connon, Stephen J</creator><creatorcontrib>Fleming, Eimear M ; Quigley, Cormac ; Rozas, Isabel ; Connon, Stephen J</creatorcontrib><description>An in silico study examined the stabilities of hydrogen-bonded complexes between simple thiourea catalysts and three different electrophiles and identified a novel, highly active N-tosyl urea catalyst for the promotion of addition reactions to epoxide electrophiles. Synthesis and evaluation of 6 revealed it to be a powerful catalyst for the addition of 1,2-dimethylindole to styrene oxide under conditions in which simple N,N-bis-aryl ureas and thioureas (including 1) are inactive. Subsequent studies determined 6 to be compatible with a range of indole and epoxide substrates (including (E)-stilbene oxide) and found that relatively poor nucleophiles such as sterically and electronically deactivated anilines, thiophenol, and benzyl alcohol could be efficiently and regioselectively added to oxiranes under mild conditions.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo702154m</identifier><identifier>PMID: 18173286</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Journal of organic chemistry, 2008-02, Vol.73 (3), p.948-956</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-8e6b8b7efcab5900f62396233ee7537a603bdfae6ed0561c8eff30d26f05e07c3</citedby><cites>FETCH-LOGICAL-a447t-8e6b8b7efcab5900f62396233ee7537a603bdfae6ed0561c8eff30d26f05e07c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo702154m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo702154m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20047504$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18173286$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fleming, Eimear M</creatorcontrib><creatorcontrib>Quigley, Cormac</creatorcontrib><creatorcontrib>Rozas, Isabel</creatorcontrib><creatorcontrib>Connon, Stephen J</creatorcontrib><title>Computational Study-Led Organocatalyst Design: A Novel, Highly Active Urea-Based Catalyst for Addition Reactions to Epoxides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An in silico study examined the stabilities of hydrogen-bonded complexes between simple thiourea catalysts and three different electrophiles and identified a novel, highly active N-tosyl urea catalyst for the promotion of addition reactions to epoxide electrophiles. Synthesis and evaluation of 6 revealed it to be a powerful catalyst for the addition of 1,2-dimethylindole to styrene oxide under conditions in which simple N,N-bis-aryl ureas and thioureas (including 1) are inactive. Subsequent studies determined 6 to be compatible with a range of indole and epoxide substrates (including (E)-stilbene oxide) and found that relatively poor nucleophiles such as sterically and electronically deactivated anilines, thiophenol, and benzyl alcohol could be efficiently and regioselectively added to oxiranes under mild conditions.</description><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNptkc9uEzEQxi0EomnhwAsgX0BCYsG7Xq-T3kLaUlBEUf9ccrFmvePgsrsOtrdqTnDlNXkSHCWkF0ayZiT_5tOnbwh5kbN3OSvy97dOpibK7hEZ5aJgWTVh5WMyYqwoMl5U_IAchnDLUgkhnpKDfJxLXoyrEfk5c91qiBCt66GlV3Fo1tkcG3rhl9A7DRHadYj0BINd9sd_fv2mU_rF3WH7lp7b5bd2Tac62jukNx4h-wAh7c7-bRnn6bRp7EadXiLozRBodPR05e5tg-EZeWKgDfh814_Izdnp9ew8m198_DSbzjMoSxmzMVb1uJZoNNRiwpipCj5JjyNKwSVUjNeNAaywYaLK9RiN4awpKsMEMqn5EXm91V1592PAEFVng8a2hR7dEFQKkEshZQLfbEHtXQgejVp524Ffq5ypTdpqn3ZiX-5Eh7rD5oHcxZuAVzsAgobWeOi1DXuuYKyUgpWJy7acDRHv9__gv6tKJl_q-uuV4peL8ixffFaLB13QIfkZfLpd-I_Bv5DGpEs</recordid><startdate>20080201</startdate><enddate>20080201</enddate><creator>Fleming, Eimear M</creator><creator>Quigley, Cormac</creator><creator>Rozas, Isabel</creator><creator>Connon, Stephen J</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080201</creationdate><title>Computational Study-Led Organocatalyst Design: A Novel, Highly Active Urea-Based Catalyst for Addition Reactions to Epoxides</title><author>Fleming, Eimear M ; Quigley, Cormac ; Rozas, Isabel ; Connon, Stephen J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-8e6b8b7efcab5900f62396233ee7537a603bdfae6ed0561c8eff30d26f05e07c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fleming, Eimear M</creatorcontrib><creatorcontrib>Quigley, Cormac</creatorcontrib><creatorcontrib>Rozas, Isabel</creatorcontrib><creatorcontrib>Connon, Stephen J</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Fleming, Eimear M</au><au>Quigley, Cormac</au><au>Rozas, Isabel</au><au>Connon, Stephen J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Computational Study-Led Organocatalyst Design: A Novel, Highly Active Urea-Based Catalyst for Addition Reactions to Epoxides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-02-01</date><risdate>2008</risdate><volume>73</volume><issue>3</issue><spage>948</spage><epage>956</epage><pages>948-956</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An in silico study examined the stabilities of hydrogen-bonded complexes between simple thiourea catalysts and three different electrophiles and identified a novel, highly active N-tosyl urea catalyst for the promotion of addition reactions to epoxide electrophiles. Synthesis and evaluation of 6 revealed it to be a powerful catalyst for the addition of 1,2-dimethylindole to styrene oxide under conditions in which simple N,N-bis-aryl ureas and thioureas (including 1) are inactive. Subsequent studies determined 6 to be compatible with a range of indole and epoxide substrates (including (E)-stilbene oxide) and found that relatively poor nucleophiles such as sterically and electronically deactivated anilines, thiophenol, and benzyl alcohol could be efficiently and regioselectively added to oxiranes under mild conditions.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18173286</pmid><doi>10.1021/jo702154m</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2008-02, Vol.73 (3), p.948-956 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70237577 |
| source | ACS Publications |
| subjects | Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Computational Study-Led Organocatalyst Design: A Novel, Highly Active Urea-Based Catalyst for Addition Reactions to Epoxides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T04%3A23%3A19IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Computational%20Study-Led%20Organocatalyst%20Design:%E2%80%89%20A%20Novel,%20Highly%20Active%20Urea-Based%20Catalyst%20for%20Addition%20Reactions%20to%20Epoxides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Fleming,%20Eimear%20M&rft.date=2008-02-01&rft.volume=73&rft.issue=3&rft.spage=948&rft.epage=956&rft.pages=948-956&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo702154m&rft_dat=%3Cproquest_cross%3E70237577%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=70237577&rft_id=info:pmid/18173286&rfr_iscdi=true |