Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols

Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols

Acyclic internal alkenes are a class of challenging substrates in asymmetric Heck-type reactions due to difficulties related to both reactivity and selectivity control. Employing acyclic alkenyl alcohols, an asymmetric Heck–Matsuda reaction is developed through the strategy of chiral anion phase tra...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2021-02, Vol.23 (4), p.1473-1477
Hauptverfasser: Zhang, Tao, Li, Wen-Ao, Shen, Hong-Cheng, Chen, Shu-Sen, Han, Zhi-Yong
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1477
container_issue 4
container_start_page 1473
container_title Organic letters
container_volume 23
creator Zhang, Tao
Li, Wen-Ao
Shen, Hong-Cheng
Chen, Shu-Sen
Han, Zhi-Yong
description Acyclic internal alkenes are a class of challenging substrates in asymmetric Heck-type reactions due to difficulties related to both reactivity and selectivity control. Employing acyclic alkenyl alcohols, an asymmetric Heck–Matsuda reaction is developed through the strategy of chiral anion phase transfer. Various chiral ketones could be obtained in high levels of enantioselectivity. A catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for the reaction to suppress the palladium-hydride-mediated side reactions.
doi_str_mv 10.1021/acs.orglett.1c00152
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2484242385</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2484242385</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-a02f917da126bc11d19b95007b299ba167e8e3c68f2f565d392e614b4fef576d3</originalsourceid><addsrcrecordid>eNp9kEtOwzAQhi0EolA4ARLKkk1aP-I8llEFFKkVEirryHEmNK0TF9tZZMcduCEnwVVLl2w81uj7ZzQfQncETwimZCqknWjzocC5CZEYE07P0JV_WZhgTs9P_xiP0LW1G4_4TnaJRoxxSlOKr9Bqtm6MUGHeNboLl1A1wkEV5HZoW3CmkcEc5Pbn63spnO0rEbyBkM6zga6DXA5SeSRXW-gG5avUa63sDbqohbJwe6xj9P70uJrNw8Xr88ssX4SCRdyFAtM6I0klCI1LSUhFsjLjGCclzbJSkDiBFJiM05rWPOYVyyjEJCqjGmqexBUbo4fD3J3Rnz1YV7SNlaCU6ED3tqBRGtGIspR7lB1QabS1BupiZ5pWmKEguNjrLLzO4qizOOr0qfvjgr5soTpl_vx5YHoA9umN7k3n7_135C-k-oRd</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2484242385</pqid></control><display><type>article</type><title>Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols</title><source>American Chemical Society Journals</source><creator>Zhang, Tao ; Li, Wen-Ao ; Shen, Hong-Cheng ; Chen, Shu-Sen ; Han, Zhi-Yong</creator><creatorcontrib>Zhang, Tao ; Li, Wen-Ao ; Shen, Hong-Cheng ; Chen, Shu-Sen ; Han, Zhi-Yong</creatorcontrib><description>Acyclic internal alkenes are a class of challenging substrates in asymmetric Heck-type reactions due to difficulties related to both reactivity and selectivity control. Employing acyclic alkenyl alcohols, an asymmetric Heck–Matsuda reaction is developed through the strategy of chiral anion phase transfer. Various chiral ketones could be obtained in high levels of enantioselectivity. A catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for the reaction to suppress the palladium-hydride-mediated side reactions.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c00152</identifier><identifier>PMID: 33522820</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2021-02, Vol.23 (4), p.1473-1477</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-a02f917da126bc11d19b95007b299ba167e8e3c68f2f565d392e614b4fef576d3</citedby><cites>FETCH-LOGICAL-a345t-a02f917da126bc11d19b95007b299ba167e8e3c68f2f565d392e614b4fef576d3</cites><orcidid>0000-0002-9225-5064</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.1c00152$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.1c00152$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33522820$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Tao</creatorcontrib><creatorcontrib>Li, Wen-Ao</creatorcontrib><creatorcontrib>Shen, Hong-Cheng</creatorcontrib><creatorcontrib>Chen, Shu-Sen</creatorcontrib><creatorcontrib>Han, Zhi-Yong</creatorcontrib><title>Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Acyclic internal alkenes are a class of challenging substrates in asymmetric Heck-type reactions due to difficulties related to both reactivity and selectivity control. Employing acyclic alkenyl alcohols, an asymmetric Heck–Matsuda reaction is developed through the strategy of chiral anion phase transfer. Various chiral ketones could be obtained in high levels of enantioselectivity. A catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for the reaction to suppress the palladium-hydride-mediated side reactions.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kEtOwzAQhi0EolA4ARLKkk1aP-I8llEFFKkVEirryHEmNK0TF9tZZMcduCEnwVVLl2w81uj7ZzQfQncETwimZCqknWjzocC5CZEYE07P0JV_WZhgTs9P_xiP0LW1G4_4TnaJRoxxSlOKr9Bqtm6MUGHeNboLl1A1wkEV5HZoW3CmkcEc5Pbn63spnO0rEbyBkM6zga6DXA5SeSRXW-gG5avUa63sDbqohbJwe6xj9P70uJrNw8Xr88ssX4SCRdyFAtM6I0klCI1LSUhFsjLjGCclzbJSkDiBFJiM05rWPOYVyyjEJCqjGmqexBUbo4fD3J3Rnz1YV7SNlaCU6ED3tqBRGtGIspR7lB1QabS1BupiZ5pWmKEguNjrLLzO4qizOOr0qfvjgr5soTpl_vx5YHoA9umN7k3n7_135C-k-oRd</recordid><startdate>20210219</startdate><enddate>20210219</enddate><creator>Zhang, Tao</creator><creator>Li, Wen-Ao</creator><creator>Shen, Hong-Cheng</creator><creator>Chen, Shu-Sen</creator><creator>Han, Zhi-Yong</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9225-5064</orcidid></search><sort><creationdate>20210219</creationdate><title>Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols</title><author>Zhang, Tao ; Li, Wen-Ao ; Shen, Hong-Cheng ; Chen, Shu-Sen ; Han, Zhi-Yong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-a02f917da126bc11d19b95007b299ba167e8e3c68f2f565d392e614b4fef576d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Tao</creatorcontrib><creatorcontrib>Li, Wen-Ao</creatorcontrib><creatorcontrib>Shen, Hong-Cheng</creatorcontrib><creatorcontrib>Chen, Shu-Sen</creatorcontrib><creatorcontrib>Han, Zhi-Yong</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, Tao</au><au>Li, Wen-Ao</au><au>Shen, Hong-Cheng</au><au>Chen, Shu-Sen</au><au>Han, Zhi-Yong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2021-02-19</date><risdate>2021</risdate><volume>23</volume><issue>4</issue><spage>1473</spage><epage>1477</epage><pages>1473-1477</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Acyclic internal alkenes are a class of challenging substrates in asymmetric Heck-type reactions due to difficulties related to both reactivity and selectivity control. Employing acyclic alkenyl alcohols, an asymmetric Heck–Matsuda reaction is developed through the strategy of chiral anion phase transfer. Various chiral ketones could be obtained in high levels of enantioselectivity. A catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for the reaction to suppress the palladium-hydride-mediated side reactions.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>33522820</pmid><doi>10.1021/acs.orglett.1c00152</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9225-5064</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2021-02, Vol.23 (4), p.1473-1477
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2484242385
source American Chemical Society Journals
title Chiral-Anion-Mediated Asymmetric Heck–Matsuda Reaction of Acyclic Alkenyl Alcohols
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T07%3A33%3A55IST&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=Chiral-Anion-Mediated%20Asymmetric%20Heck%E2%80%93Matsuda%20Reaction%20of%20Acyclic%20Alkenyl%20Alcohols&rft.jtitle=Organic%20letters&rft.au=Zhang,%20Tao&rft.date=2021-02-19&rft.volume=23&rft.issue=4&rft.spage=1473&rft.epage=1477&rft.pages=1473-1477&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c00152&rft_dat=%3Cproquest_cross%3E2484242385%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=2484242385&rft_id=info:pmid/33522820&rfr_iscdi=true