Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis
An enantioselective Mannich‐type reaction of 3‐butynol and nitrones is described, which affords dihydrofuran‐3‐ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold‐catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethe...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2018-12, Vol.57 (52), p.17200-17204 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 17204 |
|---|---|
| container_issue | 52 |
| container_start_page | 17200 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 57 |
| creator | Wei, Hanlin Bao, Ming Dong, Kuiyong Qiu, Lihua Wu, Bing Hu, Wenhao Xu, Xinfang |
| description | An enantioselective Mannich‐type reaction of 3‐butynol and nitrones is described, which affords dihydrofuran‐3‐ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold‐catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich‐type addition with the assistance of chiral phosphoric acid (CPA) and hydrogen bonding. This novel pattern of alkyne transformation involving chemical bond cleavage, and a fragment modification and reassembly process, provides an atom‐ and step‐economic method, and is the first example of cooperative asymmetric catalysis in gold‐catalyzed alkyne oxidations via an α‐oxo gold carbene route.
Golden oldie: A combination of gold(I) and chiral phosphoric acid (CPA) catalyzes a Mannich‐type reaction cooperatively. Asymmetric trapping of a gold enolate intermediate involved in alkyne oxidations occurs via an α‐oxo gold carbene route. Alkyne transformation involves 1) chemical N−O bond cleavage, 2) fragment modification, and 3) reassembly. |
| doi_str_mv | 10.1002/anie.201812140 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2127197005</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2127197005</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4100-50b203ca2ea3f9a8ed4b4e94450ae123bf8c1e898e6bd404ad594bf9cdfacc7f3</originalsourceid><addsrcrecordid>eNqFkTtPwzAURi0E4r0yokgsMKT1KzgZq6hApUIZYI4c-0Y1cuNit5Tw63FpAYmFyZ-sc4_u1YfQGcE9gjHty9ZAj2KSE0o43kGHJKMkZUKw3Zg5Y6nIM3KAjkJ4iXye4-t9dMAwExlh-BCthq1sF8YFsKAW5g2SybvR8iuVnbLmI2bX9u9l2xo1TQZam_VHEudqCzqpu-TWWX05uuqXU-OlTR6nLsynzhuVDJTRSencHPxWKRfSdsGEE7TXSBvgdPseo-eb4VN5l44nt6NyME4Vj_elGa4pZkpSkKwpZA6a1xwKzjMsgVBWN7kikBc5XNeaYy51VvC6KZRupFKiYcfocuOde_e6hLCoZiYosFa24JahooQKUgiMs4he_EFf3NK3cbtIZaLAglIRqd6GUt6F4KGp5t7MpO8qgqt1JdW6kuqnkjhwvtUu6xnoH_y7gwgUG2BlLHT_6KrBw2j4K_8EgMeZUA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2157907227</pqid></control><display><type>article</type><title>Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis</title><source>Access via Wiley Online Library</source><creator>Wei, Hanlin ; Bao, Ming ; Dong, Kuiyong ; Qiu, Lihua ; Wu, Bing ; Hu, Wenhao ; Xu, Xinfang</creator><creatorcontrib>Wei, Hanlin ; Bao, Ming ; Dong, Kuiyong ; Qiu, Lihua ; Wu, Bing ; Hu, Wenhao ; Xu, Xinfang</creatorcontrib><description>An enantioselective Mannich‐type reaction of 3‐butynol and nitrones is described, which affords dihydrofuran‐3‐ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold‐catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich‐type addition with the assistance of chiral phosphoric acid (CPA) and hydrogen bonding. This novel pattern of alkyne transformation involving chemical bond cleavage, and a fragment modification and reassembly process, provides an atom‐ and step‐economic method, and is the first example of cooperative asymmetric catalysis in gold‐catalyzed alkyne oxidations via an α‐oxo gold carbene route.
Golden oldie: A combination of gold(I) and chiral phosphoric acid (CPA) catalyzes a Mannich‐type reaction cooperatively. Asymmetric trapping of a gold enolate intermediate involved in alkyne oxidations occurs via an α‐oxo gold carbene route. Alkyne transformation involves 1) chemical N−O bond cleavage, 2) fragment modification, and 3) reassembly.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201812140</identifier><identifier>PMID: 30375130</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>alkyne oxidation ; Alkynes ; carbene ; Catalysis ; Chemical bonds ; cooperative catalysis ; Enantiomers ; enantioselective ; Gold ; Hydrogen bonding ; Mannich-type addition ; Organic chemistry ; Oxidation ; Phosphoric acid</subject><ispartof>Angewandte Chemie International Edition, 2018-12, Vol.57 (52), p.17200-17204</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4100-50b203ca2ea3f9a8ed4b4e94450ae123bf8c1e898e6bd404ad594bf9cdfacc7f3</citedby><cites>FETCH-LOGICAL-c4100-50b203ca2ea3f9a8ed4b4e94450ae123bf8c1e898e6bd404ad594bf9cdfacc7f3</cites><orcidid>0000-0002-8706-5151</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%2Fanie.201812140$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201812140$$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/30375130$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wei, Hanlin</creatorcontrib><creatorcontrib>Bao, Ming</creatorcontrib><creatorcontrib>Dong, Kuiyong</creatorcontrib><creatorcontrib>Qiu, Lihua</creatorcontrib><creatorcontrib>Wu, Bing</creatorcontrib><creatorcontrib>Hu, Wenhao</creatorcontrib><creatorcontrib>Xu, Xinfang</creatorcontrib><title>Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>An enantioselective Mannich‐type reaction of 3‐butynol and nitrones is described, which affords dihydrofuran‐3‐ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold‐catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich‐type addition with the assistance of chiral phosphoric acid (CPA) and hydrogen bonding. This novel pattern of alkyne transformation involving chemical bond cleavage, and a fragment modification and reassembly process, provides an atom‐ and step‐economic method, and is the first example of cooperative asymmetric catalysis in gold‐catalyzed alkyne oxidations via an α‐oxo gold carbene route.
Golden oldie: A combination of gold(I) and chiral phosphoric acid (CPA) catalyzes a Mannich‐type reaction cooperatively. Asymmetric trapping of a gold enolate intermediate involved in alkyne oxidations occurs via an α‐oxo gold carbene route. Alkyne transformation involves 1) chemical N−O bond cleavage, 2) fragment modification, and 3) reassembly.</description><subject>alkyne oxidation</subject><subject>Alkynes</subject><subject>carbene</subject><subject>Catalysis</subject><subject>Chemical bonds</subject><subject>cooperative catalysis</subject><subject>Enantiomers</subject><subject>enantioselective</subject><subject>Gold</subject><subject>Hydrogen bonding</subject><subject>Mannich-type addition</subject><subject>Organic chemistry</subject><subject>Oxidation</subject><subject>Phosphoric acid</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkTtPwzAURi0E4r0yokgsMKT1KzgZq6hApUIZYI4c-0Y1cuNit5Tw63FpAYmFyZ-sc4_u1YfQGcE9gjHty9ZAj2KSE0o43kGHJKMkZUKw3Zg5Y6nIM3KAjkJ4iXye4-t9dMAwExlh-BCthq1sF8YFsKAW5g2SybvR8iuVnbLmI2bX9u9l2xo1TQZam_VHEudqCzqpu-TWWX05uuqXU-OlTR6nLsynzhuVDJTRSencHPxWKRfSdsGEE7TXSBvgdPseo-eb4VN5l44nt6NyME4Vj_elGa4pZkpSkKwpZA6a1xwKzjMsgVBWN7kikBc5XNeaYy51VvC6KZRupFKiYcfocuOde_e6hLCoZiYosFa24JahooQKUgiMs4he_EFf3NK3cbtIZaLAglIRqd6GUt6F4KGp5t7MpO8qgqt1JdW6kuqnkjhwvtUu6xnoH_y7gwgUG2BlLHT_6KrBw2j4K_8EgMeZUA</recordid><startdate>20181221</startdate><enddate>20181221</enddate><creator>Wei, Hanlin</creator><creator>Bao, Ming</creator><creator>Dong, Kuiyong</creator><creator>Qiu, Lihua</creator><creator>Wu, Bing</creator><creator>Hu, Wenhao</creator><creator>Xu, Xinfang</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8706-5151</orcidid></search><sort><creationdate>20181221</creationdate><title>Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis</title><author>Wei, Hanlin ; Bao, Ming ; Dong, Kuiyong ; Qiu, Lihua ; Wu, Bing ; Hu, Wenhao ; Xu, Xinfang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4100-50b203ca2ea3f9a8ed4b4e94450ae123bf8c1e898e6bd404ad594bf9cdfacc7f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>alkyne oxidation</topic><topic>Alkynes</topic><topic>carbene</topic><topic>Catalysis</topic><topic>Chemical bonds</topic><topic>cooperative catalysis</topic><topic>Enantiomers</topic><topic>enantioselective</topic><topic>Gold</topic><topic>Hydrogen bonding</topic><topic>Mannich-type addition</topic><topic>Organic chemistry</topic><topic>Oxidation</topic><topic>Phosphoric acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wei, Hanlin</creatorcontrib><creatorcontrib>Bao, Ming</creatorcontrib><creatorcontrib>Dong, Kuiyong</creatorcontrib><creatorcontrib>Qiu, Lihua</creatorcontrib><creatorcontrib>Wu, Bing</creatorcontrib><creatorcontrib>Hu, Wenhao</creatorcontrib><creatorcontrib>Xu, Xinfang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wei, Hanlin</au><au>Bao, Ming</au><au>Dong, Kuiyong</au><au>Qiu, Lihua</au><au>Wu, Bing</au><au>Hu, Wenhao</au><au>Xu, Xinfang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-12-21</date><risdate>2018</risdate><volume>57</volume><issue>52</issue><spage>17200</spage><epage>17204</epage><pages>17200-17204</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An enantioselective Mannich‐type reaction of 3‐butynol and nitrones is described, which affords dihydrofuran‐3‐ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold‐catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich‐type addition with the assistance of chiral phosphoric acid (CPA) and hydrogen bonding. This novel pattern of alkyne transformation involving chemical bond cleavage, and a fragment modification and reassembly process, provides an atom‐ and step‐economic method, and is the first example of cooperative asymmetric catalysis in gold‐catalyzed alkyne oxidations via an α‐oxo gold carbene route.
Golden oldie: A combination of gold(I) and chiral phosphoric acid (CPA) catalyzes a Mannich‐type reaction cooperatively. Asymmetric trapping of a gold enolate intermediate involved in alkyne oxidations occurs via an α‐oxo gold carbene route. Alkyne transformation involves 1) chemical N−O bond cleavage, 2) fragment modification, and 3) reassembly.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30375130</pmid><doi>10.1002/anie.201812140</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-8706-5151</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2018-12, Vol.57 (52), p.17200-17204 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2127197005 |
| source | Access via Wiley Online Library |
| subjects | alkyne oxidation Alkynes carbene Catalysis Chemical bonds cooperative catalysis Enantiomers enantioselective Gold Hydrogen bonding Mannich-type addition Organic chemistry Oxidation Phosphoric acid |
| title | Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T16%3A28%3A01IST&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%20Oxidative%20Cyclization/Mannich%20Addition%20Enabled%20by%20Gold(I)/Chiral%20Phosphoric%20Acid%20Cooperative%20Catalysis&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Wei,%20Hanlin&rft.date=2018-12-21&rft.volume=57&rft.issue=52&rft.spage=17200&rft.epage=17204&rft.pages=17200-17204&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201812140&rft_dat=%3Cproquest_cross%3E2127197005%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=2157907227&rft_id=info:pmid/30375130&rfr_iscdi=true |