Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes
We describe a Rh(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee’s generally between 88 and 96%...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2024-09, Vol.146 (35), p.24708-24715 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 24715 |
|---|---|
| container_issue | 35 |
| container_start_page | 24708 |
| container_title | Journal of the American Chemical Society |
| container_volume | 146 |
| creator | Webster, Stephen J. Balázs, László B. Goetzke, F. Wieland Stojalnikova, Violeta Liu, Ke Christensen, Kirsten E. Mackenzie, Harold W. Fletcher, Stephen P. |
| description | We describe a Rh(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee’s generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn(OTf)2 plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods. |
| doi_str_mv | 10.1021/jacs.4c09490 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3094826619</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3094826619</sourcerecordid><originalsourceid>FETCH-LOGICAL-a249t-aff929b502300e8e79b8084b11c96f5c75ac51ebbda7dca5cb5956401359f6c63</originalsourceid><addsrcrecordid>eNptkEFLw0AQhRdRbK3ePEuOFUyd3WQ32aOEqoVCoajXsNlMakq6W7OJEH-9Ca168fQYePPezEfINYUZBUbvt0q7WahBhhJOyJhyBj6nTJySMQAwP4pFMCIXzm37MWQxPSejQFIRQCzHZLV-ny5u_UQ1quq-MPfWuCmt7ymTe3OjTFNahxXqpvxEb12ajbfaoxnUFt5babrKSzpd2X1t98qguyRnhaocXh11Ql4f5y_Js79cPS2Sh6WvWCgbXxWFZDLjwAIAjDGSWQxxmFGqpSi4jrjSnGKW5SrKteI645KLEGjAZSG0CCZkesjtiz9adE26K53GquqPsK1Lg55HzISgsrfeHay6ts7VWKT7utypuksppAPCdECYHhH29ptjcpvtMP81_zD7qx62tratTf_o_1nfmuh5Mg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3094826619</pqid></control><display><type>article</type><title>Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes</title><source>American Chemical Society Journals</source><creator>Webster, Stephen J. ; Balázs, László B. ; Goetzke, F. Wieland ; Stojalnikova, Violeta ; Liu, Ke ; Christensen, Kirsten E. ; Mackenzie, Harold W. ; Fletcher, Stephen P.</creator><creatorcontrib>Webster, Stephen J. ; Balázs, László B. ; Goetzke, F. Wieland ; Stojalnikova, Violeta ; Liu, Ke ; Christensen, Kirsten E. ; Mackenzie, Harold W. ; Fletcher, Stephen P.</creatorcontrib><description>We describe a Rh(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee’s generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn(OTf)2 plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods.</description><identifier>ISSN: 0002-7863</identifier><identifier>ISSN: 1520-5126</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.4c09490</identifier><identifier>PMID: 39163089</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2024-09, Vol.146 (35), p.24708-24715</ispartof><rights>2024 The Authors. Published by American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a249t-aff929b502300e8e79b8084b11c96f5c75ac51ebbda7dca5cb5956401359f6c63</cites><orcidid>0000-0002-2445-8417 ; 0000-0002-8688-5609 ; 0000-0003-1506-0586 ; 0000-0001-7629-0997</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jacs.4c09490$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.4c09490$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39163089$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Webster, Stephen J.</creatorcontrib><creatorcontrib>Balázs, László B.</creatorcontrib><creatorcontrib>Goetzke, F. Wieland</creatorcontrib><creatorcontrib>Stojalnikova, Violeta</creatorcontrib><creatorcontrib>Liu, Ke</creatorcontrib><creatorcontrib>Christensen, Kirsten E.</creatorcontrib><creatorcontrib>Mackenzie, Harold W.</creatorcontrib><creatorcontrib>Fletcher, Stephen P.</creatorcontrib><title>Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>We describe a Rh(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee’s generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn(OTf)2 plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods.</description><issn>0002-7863</issn><issn>1520-5126</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNptkEFLw0AQhRdRbK3ePEuOFUyd3WQ32aOEqoVCoajXsNlMakq6W7OJEH-9Ca168fQYePPezEfINYUZBUbvt0q7WahBhhJOyJhyBj6nTJySMQAwP4pFMCIXzm37MWQxPSejQFIRQCzHZLV-ny5u_UQ1quq-MPfWuCmt7ymTe3OjTFNahxXqpvxEb12ajbfaoxnUFt5babrKSzpd2X1t98qguyRnhaocXh11Ql4f5y_Js79cPS2Sh6WvWCgbXxWFZDLjwAIAjDGSWQxxmFGqpSi4jrjSnGKW5SrKteI645KLEGjAZSG0CCZkesjtiz9adE26K53GquqPsK1Lg55HzISgsrfeHay6ts7VWKT7utypuksppAPCdECYHhH29ptjcpvtMP81_zD7qx62tratTf_o_1nfmuh5Mg</recordid><startdate>20240904</startdate><enddate>20240904</enddate><creator>Webster, Stephen J.</creator><creator>Balázs, László B.</creator><creator>Goetzke, F. Wieland</creator><creator>Stojalnikova, Violeta</creator><creator>Liu, Ke</creator><creator>Christensen, Kirsten E.</creator><creator>Mackenzie, Harold W.</creator><creator>Fletcher, Stephen P.</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2445-8417</orcidid><orcidid>https://orcid.org/0000-0002-8688-5609</orcidid><orcidid>https://orcid.org/0000-0003-1506-0586</orcidid><orcidid>https://orcid.org/0000-0001-7629-0997</orcidid></search><sort><creationdate>20240904</creationdate><title>Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes</title><author>Webster, Stephen J. ; Balázs, László B. ; Goetzke, F. Wieland ; Stojalnikova, Violeta ; Liu, Ke ; Christensen, Kirsten E. ; Mackenzie, Harold W. ; Fletcher, Stephen P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a249t-aff929b502300e8e79b8084b11c96f5c75ac51ebbda7dca5cb5956401359f6c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Webster, Stephen J.</creatorcontrib><creatorcontrib>Balázs, László B.</creatorcontrib><creatorcontrib>Goetzke, F. Wieland</creatorcontrib><creatorcontrib>Stojalnikova, Violeta</creatorcontrib><creatorcontrib>Liu, Ke</creatorcontrib><creatorcontrib>Christensen, Kirsten E.</creatorcontrib><creatorcontrib>Mackenzie, Harold W.</creatorcontrib><creatorcontrib>Fletcher, Stephen P.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Webster, Stephen J.</au><au>Balázs, László B.</au><au>Goetzke, F. Wieland</au><au>Stojalnikova, Violeta</au><au>Liu, Ke</au><au>Christensen, Kirsten E.</au><au>Mackenzie, Harold W.</au><au>Fletcher, Stephen P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2024-09-04</date><risdate>2024</risdate><volume>146</volume><issue>35</issue><spage>24708</spage><epage>24715</epage><pages>24708-24715</pages><issn>0002-7863</issn><issn>1520-5126</issn><eissn>1520-5126</eissn><abstract>We describe a Rh(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee’s generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn(OTf)2 plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>39163089</pmid><doi>10.1021/jacs.4c09490</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-2445-8417</orcidid><orcidid>https://orcid.org/0000-0002-8688-5609</orcidid><orcidid>https://orcid.org/0000-0003-1506-0586</orcidid><orcidid>https://orcid.org/0000-0001-7629-0997</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2024-09, Vol.146 (35), p.24708-24715 |
| issn | 0002-7863 1520-5126 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3094826619 |
| source | American Chemical Society Journals |
| title | Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T07%3A11%3A38IST&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=Rh(I)-Catalyzed%20Regio-%20and%20Enantioselective%20Ring%20Opening%20of%20Vinyl%20Cyclopropanes&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Webster,%20Stephen%20J.&rft.date=2024-09-04&rft.volume=146&rft.issue=35&rft.spage=24708&rft.epage=24715&rft.pages=24708-24715&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.4c09490&rft_dat=%3Cproquest_cross%3E3094826619%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=3094826619&rft_id=info:pmid/39163089&rfr_iscdi=true |