Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes
A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Micha...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2015-09, Vol.21 (37), p.12885-12888 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 12888 |
|---|---|
| container_issue | 37 |
| container_start_page | 12885 |
| container_title | Chemistry : a European journal |
| container_volume | 21 |
| creator | Li, Lijun Zhang, Sheng Hu, Yanbin Li, Yanan Li, Chong Zha, Zhenggen Wang, Zhiyong |
| description | A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro‐2H‐pyrrol 4 a. Furthermore, a connection of two tridentate‐Schiff‐base subunits proved to be an effective strategy in ligand design.
Complex chemistry! A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides with unprecedented diastereoselectivity (see scheme). |
| doi_str_mv | 10.1002/chem.201502129 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1800486735</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1800486735</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5479-6519a81d173fa171b9e38d82632678d8978cb0da4f6c5106d83177f8e61d02b83</originalsourceid><addsrcrecordid>eNqFks1uEzEUhUcIRENhyxJZYtMuJvVPxvYsqyE0QWla0SKWljO-Q9x6xsGeQIbn4IFxlRIhNl35Svc7xzo6N8veEjwmGNOzeg3tmGJSYEpo-SwbkYKSnAlePM9GuJyInBesPMpexXiHMS45Yy-zI8oppoyRUfZ7Zr-t3YA-WB17COBzpDuDpp3ueusjOKh7-wPQpa3XGhw6N8amRYd8g5a2D167e91BRL1HNJ92fnD59RCssR2gZX61syYtK91rN_wCg1YDuqnTD3bbnszn89Ozym82ENJ8iirfbhzsIL7OXjTaRXjz-B5nXz5Ob6tZvri6mFfni7wuJqJMyUipJTFEsEYTQVYlMGkk5YxykYZSyHqFjZ40vC4I5kYyIkQjgROD6Uqy4-xk77sJ_vsWYq9aG2twLiXy26iIxHgiuWDF06jAkvCJkDSh7_9D7_w2dClIojgXpWCcJ2q8p-rgYwzQqE2wrQ6DIlg9VKseqlWHapPg3aPtdtWCOeB_u0xAuQd-WgfDE3aqmk0v_zXP91qbrmB30Opwr1J8Uaivywv16fNNdbtYSHXN_gAWfb2B</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1766797366</pqid></control><display><type>article</type><title>Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes</title><source>Wiley Online Library All Journals</source><creator>Li, Lijun ; Zhang, Sheng ; Hu, Yanbin ; Li, Yanan ; Li, Chong ; Zha, Zhenggen ; Wang, Zhiyong</creator><creatorcontrib>Li, Lijun ; Zhang, Sheng ; Hu, Yanbin ; Li, Yanan ; Li, Chong ; Zha, Zhenggen ; Wang, Zhiyong</creatorcontrib><description>A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro‐2H‐pyrrol 4 a. Furthermore, a connection of two tridentate‐Schiff‐base subunits proved to be an effective strategy in ligand design.
Complex chemistry! A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides with unprecedented diastereoselectivity (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201502129</identifier><identifier>PMID: 26202331</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Asymmetry ; Catalysis ; Catalysts ; Chemistry ; Design engineering ; diastereoselectivity ; Ligands ; Michael addition ; nitroalkanes ; Optical activity ; scandium ; Strategy ; Switches</subject><ispartof>Chemistry : a European journal, 2015-09, Vol.21 (37), p.12885-12888</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5479-6519a81d173fa171b9e38d82632678d8978cb0da4f6c5106d83177f8e61d02b83</citedby><cites>FETCH-LOGICAL-c5479-6519a81d173fa171b9e38d82632678d8978cb0da4f6c5106d83177f8e61d02b83</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.201502129$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201502129$$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/26202331$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Lijun</creatorcontrib><creatorcontrib>Zhang, Sheng</creatorcontrib><creatorcontrib>Hu, Yanbin</creatorcontrib><creatorcontrib>Li, Yanan</creatorcontrib><creatorcontrib>Li, Chong</creatorcontrib><creatorcontrib>Zha, Zhenggen</creatorcontrib><creatorcontrib>Wang, Zhiyong</creatorcontrib><title>Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro‐2H‐pyrrol 4 a. Furthermore, a connection of two tridentate‐Schiff‐base subunits proved to be an effective strategy in ligand design.
Complex chemistry! A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides with unprecedented diastereoselectivity (see scheme).</description><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Design engineering</subject><subject>diastereoselectivity</subject><subject>Ligands</subject><subject>Michael addition</subject><subject>nitroalkanes</subject><subject>Optical activity</subject><subject>scandium</subject><subject>Strategy</subject><subject>Switches</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFks1uEzEUhUcIRENhyxJZYtMuJvVPxvYsqyE0QWla0SKWljO-Q9x6xsGeQIbn4IFxlRIhNl35Svc7xzo6N8veEjwmGNOzeg3tmGJSYEpo-SwbkYKSnAlePM9GuJyInBesPMpexXiHMS45Yy-zI8oppoyRUfZ7Zr-t3YA-WB17COBzpDuDpp3ueusjOKh7-wPQpa3XGhw6N8amRYd8g5a2D167e91BRL1HNJ92fnD59RCssR2gZX61syYtK91rN_wCg1YDuqnTD3bbnszn89Ozym82ENJ8iirfbhzsIL7OXjTaRXjz-B5nXz5Ob6tZvri6mFfni7wuJqJMyUipJTFEsEYTQVYlMGkk5YxykYZSyHqFjZ40vC4I5kYyIkQjgROD6Uqy4-xk77sJ_vsWYq9aG2twLiXy26iIxHgiuWDF06jAkvCJkDSh7_9D7_w2dClIojgXpWCcJ2q8p-rgYwzQqE2wrQ6DIlg9VKseqlWHapPg3aPtdtWCOeB_u0xAuQd-WgfDE3aqmk0v_zXP91qbrmB30Opwr1J8Uaivywv16fNNdbtYSHXN_gAWfb2B</recordid><startdate>20150907</startdate><enddate>20150907</enddate><creator>Li, Lijun</creator><creator>Zhang, Sheng</creator><creator>Hu, Yanbin</creator><creator>Li, Yanan</creator><creator>Li, Chong</creator><creator>Zha, Zhenggen</creator><creator>Wang, Zhiyong</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>20150907</creationdate><title>Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes</title><author>Li, Lijun ; Zhang, Sheng ; Hu, Yanbin ; Li, Yanan ; Li, Chong ; Zha, Zhenggen ; Wang, Zhiyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5479-6519a81d173fa171b9e38d82632678d8978cb0da4f6c5106d83177f8e61d02b83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Design engineering</topic><topic>diastereoselectivity</topic><topic>Ligands</topic><topic>Michael addition</topic><topic>nitroalkanes</topic><topic>Optical activity</topic><topic>scandium</topic><topic>Strategy</topic><topic>Switches</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Lijun</creatorcontrib><creatorcontrib>Zhang, Sheng</creatorcontrib><creatorcontrib>Hu, Yanbin</creatorcontrib><creatorcontrib>Li, Yanan</creatorcontrib><creatorcontrib>Li, Chong</creatorcontrib><creatorcontrib>Zha, Zhenggen</creatorcontrib><creatorcontrib>Wang, Zhiyong</creatorcontrib><collection>Istex</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>Li, Lijun</au><au>Zhang, Sheng</au><au>Hu, Yanbin</au><au>Li, Yanan</au><au>Li, Chong</au><au>Zha, Zhenggen</au><au>Wang, Zhiyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2015-09-07</date><risdate>2015</risdate><volume>21</volume><issue>37</issue><spage>12885</spage><epage>12888</epage><pages>12885-12888</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro‐2H‐pyrrol 4 a. Furthermore, a connection of two tridentate‐Schiff‐base subunits proved to be an effective strategy in ligand design.
Complex chemistry! A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides with unprecedented diastereoselectivity (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26202331</pmid><doi>10.1002/chem.201502129</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2015-09, Vol.21 (37), p.12885-12888 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1800486735 |
| source | Wiley Online Library All Journals |
| subjects | Asymmetry Catalysis Catalysts Chemistry Design engineering diastereoselectivity Ligands Michael addition nitroalkanes Optical activity scandium Strategy Switches |
| title | Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T05%3A07%3A45IST&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=Highly%20Diastereo-%20and%20Enantioselective%20Michael%20Addition%20of%20Nitroalkanes%20to%202-Enoyl-Pyridine%20N-Oxides%20Catalyzed%20by%20Scandium(III)/Copper(II)%20Complexes&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Li,%20Lijun&rft.date=2015-09-07&rft.volume=21&rft.issue=37&rft.spage=12885&rft.epage=12888&rft.pages=12885-12888&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201502129&rft_dat=%3Cproquest_cross%3E1800486735%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=1766797366&rft_id=info:pmid/26202331&rfr_iscdi=true |