Enantioselective Synthesis of 3‐Hydroxy‐2‐Oxindoles via Ni‐Catalyzed Asymmetric Addition of Aromatic Bromides to α‐Ketoamides
Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to afford chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containin...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2024-12, Vol.30 (72), p.e202403622-n/a |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | n/a |
|---|---|
| container_issue | 72 |
| container_start_page | e202403622 |
| container_title | Chemistry : a European journal |
| container_volume | 30 |
| creator | Tian, Jiangyan Li, Xuening Shou, Tao Li, Wendian Lv, Hui |
| description | Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to afford chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core. The gram‐scale reaction proved the potential utility of the methodology.
Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to yield chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core. |
| doi_str_mv | 10.1002/chem.202403622 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3116678787</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3116678787</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2982-69d397fb26d5e732faf035a536cefbc281c238d89683cd1e7f520cff79d027c83</originalsourceid><addsrcrecordid>eNqFkc1uEzEUha0KRNOUbZdoJDZsJvgn47GXIQoN6t-isB459rXqamZcbKftdNUlS16FF-EheJI6TVskNsiyfHX0naMrH4QOCJ4QjOlHfQHdhGI6xYxTuoNGpKKkZDWvXqERltO65BWTu2gvxkuMseSMvUG7TGZeVGKEfix61SfnI7Sgk7uG4nzo0wVEFwtvC_bn_udyMMHfDnmi-Z7dut74FmJx7VRx6rI0V0m1wx2YYhaHroMUnC5mxric229SZsF3KmXxUx6cyd7ki9-_svUIkleP0j56bVUb4e3TO0bfPi--zpfl8dnhl_nsuNRUClpyaZis7YpyU0HNqFUWs0pVjGuwK00F0ZQJIyQXTBsCta0o1tbW0mBaa8HG6MM29yr472uIqelc1NC2qge_jg0jhPNa5JPR9_-gl34d-rxdpqaCCcHyf47RZEvp4GMMYJur4DoVhobgZtNRs-moeekoG949xa5XHZgX_LmUDMgtcONaGP4T18yXi5O_4Q_kYqS9</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3148388396</pqid></control><display><type>article</type><title>Enantioselective Synthesis of 3‐Hydroxy‐2‐Oxindoles via Ni‐Catalyzed Asymmetric Addition of Aromatic Bromides to α‐Ketoamides</title><source>Wiley-Blackwell Journals</source><creator>Tian, Jiangyan ; Li, Xuening ; Shou, Tao ; Li, Wendian ; Lv, Hui</creator><creatorcontrib>Tian, Jiangyan ; Li, Xuening ; Shou, Tao ; Li, Wendian ; Lv, Hui</creatorcontrib><description>Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to afford chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core. The gram‐scale reaction proved the potential utility of the methodology.
Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to yield chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core.</description><identifier>ISSN: 0947-6539</identifier><identifier>ISSN: 1521-3765</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202403622</identifier><identifier>PMID: 39403858</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Asymmetric addition ; Asymmetry ; Bromides ; Chemical synthesis ; Enantiomers ; Halides ; Hydroxyl oxindole ; Ketoamides ; Nickel ; Reductive coupling</subject><ispartof>Chemistry : a European journal, 2024-12, Vol.30 (72), p.e202403622-n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><rights>2024 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2982-69d397fb26d5e732faf035a536cefbc281c238d89683cd1e7f520cff79d027c83</cites><orcidid>0000-0003-1378-1945</orcidid></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.202403622$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202403622$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39403858$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tian, Jiangyan</creatorcontrib><creatorcontrib>Li, Xuening</creatorcontrib><creatorcontrib>Shou, Tao</creatorcontrib><creatorcontrib>Li, Wendian</creatorcontrib><creatorcontrib>Lv, Hui</creatorcontrib><title>Enantioselective Synthesis of 3‐Hydroxy‐2‐Oxindoles via Ni‐Catalyzed Asymmetric Addition of Aromatic Bromides to α‐Ketoamides</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to afford chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core. The gram‐scale reaction proved the potential utility of the methodology.
Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to yield chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core.</description><subject>Asymmetric addition</subject><subject>Asymmetry</subject><subject>Bromides</subject><subject>Chemical synthesis</subject><subject>Enantiomers</subject><subject>Halides</subject><subject>Hydroxyl oxindole</subject><subject>Ketoamides</subject><subject>Nickel</subject><subject>Reductive coupling</subject><issn>0947-6539</issn><issn>1521-3765</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkc1uEzEUha0KRNOUbZdoJDZsJvgn47GXIQoN6t-isB459rXqamZcbKftdNUlS16FF-EheJI6TVskNsiyfHX0naMrH4QOCJ4QjOlHfQHdhGI6xYxTuoNGpKKkZDWvXqERltO65BWTu2gvxkuMseSMvUG7TGZeVGKEfix61SfnI7Sgk7uG4nzo0wVEFwtvC_bn_udyMMHfDnmi-Z7dut74FmJx7VRx6rI0V0m1wx2YYhaHroMUnC5mxric229SZsF3KmXxUx6cyd7ki9-_svUIkleP0j56bVUb4e3TO0bfPi--zpfl8dnhl_nsuNRUClpyaZis7YpyU0HNqFUWs0pVjGuwK00F0ZQJIyQXTBsCta0o1tbW0mBaa8HG6MM29yr472uIqelc1NC2qge_jg0jhPNa5JPR9_-gl34d-rxdpqaCCcHyf47RZEvp4GMMYJur4DoVhobgZtNRs-moeekoG949xa5XHZgX_LmUDMgtcONaGP4T18yXi5O_4Q_kYqS9</recordid><startdate>20241223</startdate><enddate>20241223</enddate><creator>Tian, Jiangyan</creator><creator>Li, Xuening</creator><creator>Shou, Tao</creator><creator>Li, Wendian</creator><creator>Lv, Hui</creator><general>Wiley Subscription Services, Inc</general><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><orcidid>https://orcid.org/0000-0003-1378-1945</orcidid></search><sort><creationdate>20241223</creationdate><title>Enantioselective Synthesis of 3‐Hydroxy‐2‐Oxindoles via Ni‐Catalyzed Asymmetric Addition of Aromatic Bromides to α‐Ketoamides</title><author>Tian, Jiangyan ; Li, Xuening ; Shou, Tao ; Li, Wendian ; Lv, Hui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2982-69d397fb26d5e732faf035a536cefbc281c238d89683cd1e7f520cff79d027c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Asymmetric addition</topic><topic>Asymmetry</topic><topic>Bromides</topic><topic>Chemical synthesis</topic><topic>Enantiomers</topic><topic>Halides</topic><topic>Hydroxyl oxindole</topic><topic>Ketoamides</topic><topic>Nickel</topic><topic>Reductive coupling</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tian, Jiangyan</creatorcontrib><creatorcontrib>Li, Xuening</creatorcontrib><creatorcontrib>Shou, Tao</creatorcontrib><creatorcontrib>Li, Wendian</creatorcontrib><creatorcontrib>Lv, Hui</creatorcontrib><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>Tian, Jiangyan</au><au>Li, Xuening</au><au>Shou, Tao</au><au>Li, Wendian</au><au>Lv, Hui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of 3‐Hydroxy‐2‐Oxindoles via Ni‐Catalyzed Asymmetric Addition of Aromatic Bromides to α‐Ketoamides</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2024-12-23</date><risdate>2024</risdate><volume>30</volume><issue>72</issue><spage>e202403622</spage><epage>n/a</epage><pages>e202403622-n/a</pages><issn>0947-6539</issn><issn>1521-3765</issn><eissn>1521-3765</eissn><abstract>Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to afford chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core. The gram‐scale reaction proved the potential utility of the methodology.
Nickel‐catalyzed asymmetric intramolecular addition of aryl halides to α‐ketoamides has been achieved to yield chiral 3‐substituted‐3‐hydroxy‐2‐oxindoles in excellent yields and high enantioselectivities (up to 99 % yield and 98 % ee), which provides efficient access to valuable molecules containing 3‐hydroxy‐2‐oxindole core.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>39403858</pmid><doi>10.1002/chem.202403622</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-1378-1945</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2024-12, Vol.30 (72), p.e202403622-n/a |
| issn | 0947-6539 1521-3765 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3116678787 |
| source | Wiley-Blackwell Journals |
| subjects | Asymmetric addition Asymmetry Bromides Chemical synthesis Enantiomers Halides Hydroxyl oxindole Ketoamides Nickel Reductive coupling |
| title | Enantioselective Synthesis of 3‐Hydroxy‐2‐Oxindoles via Ni‐Catalyzed Asymmetric Addition of Aromatic Bromides to α‐Ketoamides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T14%3A24%3A56IST&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%20Synthesis%20of%203%E2%80%90Hydroxy%E2%80%902%E2%80%90Oxindoles%20via%20Ni%E2%80%90Catalyzed%20Asymmetric%20Addition%20of%20Aromatic%20Bromides%20to%20%CE%B1%E2%80%90Ketoamides&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Tian,%20Jiangyan&rft.date=2024-12-23&rft.volume=30&rft.issue=72&rft.spage=e202403622&rft.epage=n/a&rft.pages=e202403622-n/a&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.202403622&rft_dat=%3Cproquest_cross%3E3116678787%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=3148388396&rft_id=info:pmid/39403858&rfr_iscdi=true |