Enantioselective nitro-Michael reactions catalyzed by short peptides on water
Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2009-01, Vol.7 (20), p.4279-4284 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4284 |
|---|---|
| container_issue | 20 |
| container_start_page | 4279 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 7 |
| creator | Freund, Matthias Schenker, Sebastian Tsogoeva, Svetlana B |
| description | Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent. |
| doi_str_mv | 10.1039/b910249c |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_734068407</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>734068407</sourcerecordid><originalsourceid>FETCH-LOGICAL-c348t-917692e23ffd40486cf8b0fd8abf1b97e559b4d68302f61b8fdea56824a5f7fa3</originalsourceid><addsrcrecordid>eNpFkE1LAzEURYMotlbBXyDZ6WY0mWQmyVKkfkCLG10PSeaFRqaTMUmV-usdadXVvTwOF95B6JySa0qYujGKkpIre4CmlAtRkIqpw79ekgk6SemNEKpEzY_RZExVkVpO0XLe6z77kKADm_0H4N7nGIqltysNHY6gx3PoE7Y66277BS02W5xWIWY8wJB9CwmHHn_qDPEUHTndJTjb5wy93s9f7h6LxfPD093torCMy1woKmpVQsmcaznhsrZOGuJaqY2jRgmoKmV4W0tGSldTI10LuqplyXXlhNNshi53u0MM7xtIuVn7ZKHrdA9hkxrB-PgdJ2Ikr3akjSGlCK4Zol_ruG0oaX7cNb_uRvRiP7oxa2j_wb0s9g1D7Gpg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>734068407</pqid></control><display><type>article</type><title>Enantioselective nitro-Michael reactions catalyzed by short peptides on water</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Freund, Matthias ; Schenker, Sebastian ; Tsogoeva, Svetlana B</creator><creatorcontrib>Freund, Matthias ; Schenker, Sebastian ; Tsogoeva, Svetlana B</creatorcontrib><description>Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b910249c</identifier><identifier>PMID: 19795068</identifier><language>eng</language><publisher>England</publisher><subject>Catalysis ; Ketones - chemistry ; Oligopeptides - chemistry ; Proline ; Stereoisomerism ; Styrene - chemistry ; Substrate Specificity ; Water - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2009-01, Vol.7 (20), p.4279-4284</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c348t-917692e23ffd40486cf8b0fd8abf1b97e559b4d68302f61b8fdea56824a5f7fa3</citedby><cites>FETCH-LOGICAL-c348t-917692e23ffd40486cf8b0fd8abf1b97e559b4d68302f61b8fdea56824a5f7fa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19795068$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Freund, Matthias</creatorcontrib><creatorcontrib>Schenker, Sebastian</creatorcontrib><creatorcontrib>Tsogoeva, Svetlana B</creatorcontrib><title>Enantioselective nitro-Michael reactions catalyzed by short peptides on water</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent.</description><subject>Catalysis</subject><subject>Ketones - chemistry</subject><subject>Oligopeptides - chemistry</subject><subject>Proline</subject><subject>Stereoisomerism</subject><subject>Styrene - chemistry</subject><subject>Substrate Specificity</subject><subject>Water - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1LAzEURYMotlbBXyDZ6WY0mWQmyVKkfkCLG10PSeaFRqaTMUmV-usdadXVvTwOF95B6JySa0qYujGKkpIre4CmlAtRkIqpw79ekgk6SemNEKpEzY_RZExVkVpO0XLe6z77kKADm_0H4N7nGIqltysNHY6gx3PoE7Y66277BS02W5xWIWY8wJB9CwmHHn_qDPEUHTndJTjb5wy93s9f7h6LxfPD093torCMy1woKmpVQsmcaznhsrZOGuJaqY2jRgmoKmV4W0tGSldTI10LuqplyXXlhNNshi53u0MM7xtIuVn7ZKHrdA9hkxrB-PgdJ2Ikr3akjSGlCK4Zol_ruG0oaX7cNb_uRvRiP7oxa2j_wb0s9g1D7Gpg</recordid><startdate>20090101</startdate><enddate>20090101</enddate><creator>Freund, Matthias</creator><creator>Schenker, Sebastian</creator><creator>Tsogoeva, Svetlana B</creator><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>20090101</creationdate><title>Enantioselective nitro-Michael reactions catalyzed by short peptides on water</title><author>Freund, Matthias ; Schenker, Sebastian ; Tsogoeva, Svetlana B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c348t-917692e23ffd40486cf8b0fd8abf1b97e559b4d68302f61b8fdea56824a5f7fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Catalysis</topic><topic>Ketones - chemistry</topic><topic>Oligopeptides - chemistry</topic><topic>Proline</topic><topic>Stereoisomerism</topic><topic>Styrene - chemistry</topic><topic>Substrate Specificity</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Freund, Matthias</creatorcontrib><creatorcontrib>Schenker, Sebastian</creatorcontrib><creatorcontrib>Tsogoeva, Svetlana B</creatorcontrib><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>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Freund, Matthias</au><au>Schenker, Sebastian</au><au>Tsogoeva, Svetlana B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective nitro-Michael reactions catalyzed by short peptides on water</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2009-01-01</date><risdate>2009</risdate><volume>7</volume><issue>20</issue><spage>4279</spage><epage>4284</epage><pages>4279-4284</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent.</abstract><cop>England</cop><pmid>19795068</pmid><doi>10.1039/b910249c</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2009-01, Vol.7 (20), p.4279-4284 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_734068407 |
| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Catalysis Ketones - chemistry Oligopeptides - chemistry Proline Stereoisomerism Styrene - chemistry Substrate Specificity Water - chemistry |
| title | Enantioselective nitro-Michael reactions catalyzed by short peptides on water |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T23%3A45%3A30IST&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=Enantioselective%20nitro-Michael%20reactions%20catalyzed%20by%20short%20peptides%20on%20water&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Freund,%20Matthias&rft.date=2009-01-01&rft.volume=7&rft.issue=20&rft.spage=4279&rft.epage=4284&rft.pages=4279-4284&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/b910249c&rft_dat=%3Cproquest_cross%3E734068407%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=734068407&rft_id=info:pmid/19795068&rfr_iscdi=true |