Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)‑ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis

An asymmetric dual-metal relay catalysis strategy that combines Rh/chiral sulfur-olefin-catalyzed enantioselective 1,2-addition with a Pd-catalyzed intramolecular C–O coupling has been developed. The method allows rapid and efficient synthesis of quaternary carbon-containing gem-diaryl benzofuran-3­...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2017-05, Vol.19 (10), p.2726-2729
Hauptverfasser: Zhang, Zong-Feng, Zhu, Dong-Xing, Chen, Wen-Wen, Xu, Bin, Xu, Ming-Hua
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2729
container_issue 10
container_start_page 2726
container_title Organic letters
container_volume 19
creator Zhang, Zong-Feng
Zhu, Dong-Xing
Chen, Wen-Wen
Xu, Bin
Xu, Ming-Hua
description An asymmetric dual-metal relay catalysis strategy that combines Rh/chiral sulfur-olefin-catalyzed enantioselective 1,2-addition with a Pd-catalyzed intramolecular C–O coupling has been developed. The method allows rapid and efficient synthesis of quaternary carbon-containing gem-diaryl benzofuran-3­(2H)-ones in good yields in a highly enantioselective manner (up to 99% ee) through a simple one-pot cascade reaction.
doi_str_mv 10.1021/acs.orglett.7b01070
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1896895620</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1896895620</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-93ec81e4ada209353579d27a18c053d72a866a99d27d7bdf3eb1dede626077103</originalsourceid><addsrcrecordid>eNp9kE1u2zAQhYmgQZO6PUGAgstkIZs_ligtU8eNCxhI4CZrYSyOEgYSmZKUAXXVK_SKPUkk2PUyqxkM3nsz8xFywdmUM8FnUIWp808NxjhVW8aZYifknKdCJoql4sOxz9gZ-RTCC2N8mBQfyZnI53nK5_k56ZcWbDQuYINVNDukP3sbnzGYQF1Nn7BNbgz4vqHf0P52defBJvJSrK7-_fnrLAa6M0DvLCb3LtLr0LctRm8qunl22nTt7B6aBsaObrCBni4gQtMP8Z_JaQ1NwC-HOiGP35cPi1Wyvrv9sbheJyDnaUwKiVXOcQ4aBCtkKlNVaKGA5xVLpVYC8iyDYpxptdW1xC3XqDETGVOKMzkhl_vcV-9-dRhi2ZpQ4XCVRdeFkudFlhdpJkap3Esr70LwWJev3rTD9yVn5ci8HJiXB-blgfng-npY0G1b1EfPf8iDYLYXjO4X13k7_Ptu5BsG0ZJJ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1896895620</pqid></control><display><type>article</type><title>Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)‑ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis</title><source>ACS Publications</source><creator>Zhang, Zong-Feng ; Zhu, Dong-Xing ; Chen, Wen-Wen ; Xu, Bin ; Xu, Ming-Hua</creator><creatorcontrib>Zhang, Zong-Feng ; Zhu, Dong-Xing ; Chen, Wen-Wen ; Xu, Bin ; Xu, Ming-Hua</creatorcontrib><description>An asymmetric dual-metal relay catalysis strategy that combines Rh/chiral sulfur-olefin-catalyzed enantioselective 1,2-addition with a Pd-catalyzed intramolecular C–O coupling has been developed. The method allows rapid and efficient synthesis of quaternary carbon-containing gem-diaryl benzofuran-3­(2H)-ones in good yields in a highly enantioselective manner (up to 99% ee) through a simple one-pot cascade reaction.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.7b01070</identifier><identifier>PMID: 28485148</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2017-05, Vol.19 (10), p.2726-2729</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-93ec81e4ada209353579d27a18c053d72a866a99d27d7bdf3eb1dede626077103</citedby><cites>FETCH-LOGICAL-a345t-93ec81e4ada209353579d27a18c053d72a866a99d27d7bdf3eb1dede626077103</cites><orcidid>0000-0002-1692-2718 ; 0000-0002-9251-6930</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/acs.orglett.7b01070$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.7b01070$$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/28485148$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Zong-Feng</creatorcontrib><creatorcontrib>Zhu, Dong-Xing</creatorcontrib><creatorcontrib>Chen, Wen-Wen</creatorcontrib><creatorcontrib>Xu, Bin</creatorcontrib><creatorcontrib>Xu, Ming-Hua</creatorcontrib><title>Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)‑ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An asymmetric dual-metal relay catalysis strategy that combines Rh/chiral sulfur-olefin-catalyzed enantioselective 1,2-addition with a Pd-catalyzed intramolecular C–O coupling has been developed. The method allows rapid and efficient synthesis of quaternary carbon-containing gem-diaryl benzofuran-3­(2H)-ones in good yields in a highly enantioselective manner (up to 99% ee) through a simple one-pot cascade reaction.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kE1u2zAQhYmgQZO6PUGAgstkIZs_ligtU8eNCxhI4CZrYSyOEgYSmZKUAXXVK_SKPUkk2PUyqxkM3nsz8xFywdmUM8FnUIWp808NxjhVW8aZYifknKdCJoql4sOxz9gZ-RTCC2N8mBQfyZnI53nK5_k56ZcWbDQuYINVNDukP3sbnzGYQF1Nn7BNbgz4vqHf0P52defBJvJSrK7-_fnrLAa6M0DvLCb3LtLr0LctRm8qunl22nTt7B6aBsaObrCBni4gQtMP8Z_JaQ1NwC-HOiGP35cPi1Wyvrv9sbheJyDnaUwKiVXOcQ4aBCtkKlNVaKGA5xVLpVYC8iyDYpxptdW1xC3XqDETGVOKMzkhl_vcV-9-dRhi2ZpQ4XCVRdeFkudFlhdpJkap3Esr70LwWJev3rTD9yVn5ci8HJiXB-blgfng-npY0G1b1EfPf8iDYLYXjO4X13k7_Ptu5BsG0ZJJ</recordid><startdate>20170519</startdate><enddate>20170519</enddate><creator>Zhang, Zong-Feng</creator><creator>Zhu, Dong-Xing</creator><creator>Chen, Wen-Wen</creator><creator>Xu, Bin</creator><creator>Xu, Ming-Hua</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1692-2718</orcidid><orcidid>https://orcid.org/0000-0002-9251-6930</orcidid></search><sort><creationdate>20170519</creationdate><title>Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)‑ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis</title><author>Zhang, Zong-Feng ; Zhu, Dong-Xing ; Chen, Wen-Wen ; Xu, Bin ; Xu, Ming-Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-93ec81e4ada209353579d27a18c053d72a866a99d27d7bdf3eb1dede626077103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zong-Feng</creatorcontrib><creatorcontrib>Zhu, Dong-Xing</creatorcontrib><creatorcontrib>Chen, Wen-Wen</creatorcontrib><creatorcontrib>Xu, Bin</creatorcontrib><creatorcontrib>Xu, Ming-Hua</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Zong-Feng</au><au>Zhu, Dong-Xing</au><au>Chen, Wen-Wen</au><au>Xu, Bin</au><au>Xu, Ming-Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)‑ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2017-05-19</date><risdate>2017</risdate><volume>19</volume><issue>10</issue><spage>2726</spage><epage>2729</epage><pages>2726-2729</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An asymmetric dual-metal relay catalysis strategy that combines Rh/chiral sulfur-olefin-catalyzed enantioselective 1,2-addition with a Pd-catalyzed intramolecular C–O coupling has been developed. The method allows rapid and efficient synthesis of quaternary carbon-containing gem-diaryl benzofuran-3­(2H)-ones in good yields in a highly enantioselective manner (up to 99% ee) through a simple one-pot cascade reaction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28485148</pmid><doi>10.1021/acs.orglett.7b01070</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-1692-2718</orcidid><orcidid>https://orcid.org/0000-0002-9251-6930</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2017-05, Vol.19 (10), p.2726-2729
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1896895620
source ACS Publications
title Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)‑ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T17%3A43%3A19IST&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%20gem-Diaryl%20Benzofuran-3(2H)%E2%80%91ones%20via%20One-Pot%20Asymmetric%20Rhodium/Palladium%20Relay%20Catalysis&rft.jtitle=Organic%20letters&rft.au=Zhang,%20Zong-Feng&rft.date=2017-05-19&rft.volume=19&rft.issue=10&rft.spage=2726&rft.epage=2729&rft.pages=2726-2729&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.7b01070&rft_dat=%3Cproquest_cross%3E1896895620%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=1896895620&rft_id=info:pmid/28485148&rfr_iscdi=true