Anti‐Markovnikov Hydroamination and Hydroalkoxylation of Allylic Alcohols Promoted by a Simple Rare‐Earth Metal Trialkyl Complex

An exclusive anti‐Markovnikov hydroamination as well as hydroalkoxylation of allylic alcohols catalyzed by a simple catalyst Y(CH2SiMe3)3(THF)2 has been developed, providing a variety of γ‐amino and γ‐alkoxy alcohols in good yields under mild conditions. Moreover, this protocol is applied to the syn...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2024-03, Vol.366 (6), p.1405-1411
Hauptverfasser: Zhu, Xiancui, Sun, Jinrong, Wu, Zhixin, Guo, Dianjun, Zhou, Shuangliu, Wang, Shaowu
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1411
container_issue 6
container_start_page 1405
container_title Advanced synthesis & catalysis
container_volume 366
creator Zhu, Xiancui
Sun, Jinrong
Wu, Zhixin
Guo, Dianjun
Zhou, Shuangliu
Wang, Shaowu
description An exclusive anti‐Markovnikov hydroamination as well as hydroalkoxylation of allylic alcohols catalyzed by a simple catalyst Y(CH2SiMe3)3(THF)2 has been developed, providing a variety of γ‐amino and γ‐alkoxy alcohols in good yields under mild conditions. Moreover, this protocol is applied to the synthesis of drug molecules Propipocaine and Proroxan. The rare‐earth metal catalyst features readily available, wide substrate compatability, exclusive anti‐Markovnikov selectivity, and performs in the absence of a base or an additive.
doi_str_mv 10.1002/adsc.202301142
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2998629319</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2998629319</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3172-74f7e933ab49d91dafb2919e35155c79da5165740a4f0e54c97f5d580a74289f3</originalsourceid><addsrcrecordid>eNqFUE9PwjAcXYwmInr13MTzsO3adT0uiGIC0Qiel7J2odCt2A5lNw9-AD-jn8SRETx6-b1fXt6f5AXBNYIDBCG-FdLnAwxxBBEi-CTooRjRkKCYnx5_Cs-DC-9XECKWMNYLvtKq1j-f31Ph1va90u0B40Y6K0pdiVrbCohKHiiztrvGdKwtQGpMY3TeYm6X1njw7GxpayXBogECzHS5MQq8CKfagpFw9RJMVS0MmDvdZjUGDO1esrsMzgphvLo6YD94vR_Nh-Nw8vTwOEwnYR4hhkNGCqZ4FIkF4ZIjKYoF5oiriCJKc8aloCimjEBBCqgoyTkrqKQJFIzghBdRP7jpcjfOvm2Vr7OV3bqqrcww50mMeYR4qxp0qtxZ750qso3TpXBNhmC2XzrbL50dl24NvDN8aKOaf9RZejcb_nl_AYURhbg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2998629319</pqid></control><display><type>article</type><title>Anti‐Markovnikov Hydroamination and Hydroalkoxylation of Allylic Alcohols Promoted by a Simple Rare‐Earth Metal Trialkyl Complex</title><source>Wiley-Blackwell Journals</source><creator>Zhu, Xiancui ; Sun, Jinrong ; Wu, Zhixin ; Guo, Dianjun ; Zhou, Shuangliu ; Wang, Shaowu</creator><creatorcontrib>Zhu, Xiancui ; Sun, Jinrong ; Wu, Zhixin ; Guo, Dianjun ; Zhou, Shuangliu ; Wang, Shaowu</creatorcontrib><description>An exclusive anti‐Markovnikov hydroamination as well as hydroalkoxylation of allylic alcohols catalyzed by a simple catalyst Y(CH2SiMe3)3(THF)2 has been developed, providing a variety of γ‐amino and γ‐alkoxy alcohols in good yields under mild conditions. Moreover, this protocol is applied to the synthesis of drug molecules Propipocaine and Proroxan. The rare‐earth metal catalyst features readily available, wide substrate compatability, exclusive anti‐Markovnikov selectivity, and performs in the absence of a base or an additive.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202301142</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; allylic alcohols ; Catalysts ; Chemical synthesis ; hydroalkoxylation ; hydroamination ; rare-earth metal catalysts ; Substrates ; γ-functionalized alcohols</subject><ispartof>Advanced synthesis &amp; catalysis, 2024-03, Vol.366 (6), p.1405-1411</ispartof><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3172-74f7e933ab49d91dafb2919e35155c79da5165740a4f0e54c97f5d580a74289f3</citedby><cites>FETCH-LOGICAL-c3172-74f7e933ab49d91dafb2919e35155c79da5165740a4f0e54c97f5d580a74289f3</cites><orcidid>0000-0001-7354-3573</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%2Fadsc.202301142$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202301142$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Zhu, Xiancui</creatorcontrib><creatorcontrib>Sun, Jinrong</creatorcontrib><creatorcontrib>Wu, Zhixin</creatorcontrib><creatorcontrib>Guo, Dianjun</creatorcontrib><creatorcontrib>Zhou, Shuangliu</creatorcontrib><creatorcontrib>Wang, Shaowu</creatorcontrib><title>Anti‐Markovnikov Hydroamination and Hydroalkoxylation of Allylic Alcohols Promoted by a Simple Rare‐Earth Metal Trialkyl Complex</title><title>Advanced synthesis &amp; catalysis</title><description>An exclusive anti‐Markovnikov hydroamination as well as hydroalkoxylation of allylic alcohols catalyzed by a simple catalyst Y(CH2SiMe3)3(THF)2 has been developed, providing a variety of γ‐amino and γ‐alkoxy alcohols in good yields under mild conditions. Moreover, this protocol is applied to the synthesis of drug molecules Propipocaine and Proroxan. The rare‐earth metal catalyst features readily available, wide substrate compatability, exclusive anti‐Markovnikov selectivity, and performs in the absence of a base or an additive.</description><subject>Alcohols</subject><subject>allylic alcohols</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>hydroalkoxylation</subject><subject>hydroamination</subject><subject>rare-earth metal catalysts</subject><subject>Substrates</subject><subject>γ-functionalized alcohols</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFUE9PwjAcXYwmInr13MTzsO3adT0uiGIC0Qiel7J2odCt2A5lNw9-AD-jn8SRETx6-b1fXt6f5AXBNYIDBCG-FdLnAwxxBBEi-CTooRjRkKCYnx5_Cs-DC-9XECKWMNYLvtKq1j-f31Ph1va90u0B40Y6K0pdiVrbCohKHiiztrvGdKwtQGpMY3TeYm6X1njw7GxpayXBogECzHS5MQq8CKfagpFw9RJMVS0MmDvdZjUGDO1esrsMzgphvLo6YD94vR_Nh-Nw8vTwOEwnYR4hhkNGCqZ4FIkF4ZIjKYoF5oiriCJKc8aloCimjEBBCqgoyTkrqKQJFIzghBdRP7jpcjfOvm2Vr7OV3bqqrcww50mMeYR4qxp0qtxZ750qso3TpXBNhmC2XzrbL50dl24NvDN8aKOaf9RZejcb_nl_AYURhbg</recordid><startdate>20240319</startdate><enddate>20240319</enddate><creator>Zhu, Xiancui</creator><creator>Sun, Jinrong</creator><creator>Wu, Zhixin</creator><creator>Guo, Dianjun</creator><creator>Zhou, Shuangliu</creator><creator>Wang, Shaowu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-7354-3573</orcidid></search><sort><creationdate>20240319</creationdate><title>Anti‐Markovnikov Hydroamination and Hydroalkoxylation of Allylic Alcohols Promoted by a Simple Rare‐Earth Metal Trialkyl Complex</title><author>Zhu, Xiancui ; Sun, Jinrong ; Wu, Zhixin ; Guo, Dianjun ; Zhou, Shuangliu ; Wang, Shaowu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3172-74f7e933ab49d91dafb2919e35155c79da5165740a4f0e54c97f5d580a74289f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alcohols</topic><topic>allylic alcohols</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>hydroalkoxylation</topic><topic>hydroamination</topic><topic>rare-earth metal catalysts</topic><topic>Substrates</topic><topic>γ-functionalized alcohols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Xiancui</creatorcontrib><creatorcontrib>Sun, Jinrong</creatorcontrib><creatorcontrib>Wu, Zhixin</creatorcontrib><creatorcontrib>Guo, Dianjun</creatorcontrib><creatorcontrib>Zhou, Shuangliu</creatorcontrib><creatorcontrib>Wang, Shaowu</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Xiancui</au><au>Sun, Jinrong</au><au>Wu, Zhixin</au><au>Guo, Dianjun</au><au>Zhou, Shuangliu</au><au>Wang, Shaowu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti‐Markovnikov Hydroamination and Hydroalkoxylation of Allylic Alcohols Promoted by a Simple Rare‐Earth Metal Trialkyl Complex</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><date>2024-03-19</date><risdate>2024</risdate><volume>366</volume><issue>6</issue><spage>1405</spage><epage>1411</epage><pages>1405-1411</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An exclusive anti‐Markovnikov hydroamination as well as hydroalkoxylation of allylic alcohols catalyzed by a simple catalyst Y(CH2SiMe3)3(THF)2 has been developed, providing a variety of γ‐amino and γ‐alkoxy alcohols in good yields under mild conditions. Moreover, this protocol is applied to the synthesis of drug molecules Propipocaine and Proroxan. The rare‐earth metal catalyst features readily available, wide substrate compatability, exclusive anti‐Markovnikov selectivity, and performs in the absence of a base or an additive.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202301142</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7354-3573</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2024-03, Vol.366 (6), p.1405-1411
issn 1615-4150
1615-4169
language eng
recordid cdi_proquest_journals_2998629319
source Wiley-Blackwell Journals
subjects Alcohols
allylic alcohols
Catalysts
Chemical synthesis
hydroalkoxylation
hydroamination
rare-earth metal catalysts
Substrates
γ-functionalized alcohols
title Anti‐Markovnikov Hydroamination and Hydroalkoxylation of Allylic Alcohols Promoted by a Simple Rare‐Earth Metal Trialkyl Complex
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-11T18%3A33%3A12IST&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=Anti%E2%80%90Markovnikov%20Hydroamination%20and%20Hydroalkoxylation%20of%20Allylic%20Alcohols%20Promoted%20by%20a%20Simple%20Rare%E2%80%90Earth%20Metal%20Trialkyl%20Complex&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Zhu,%20Xiancui&rft.date=2024-03-19&rft.volume=366&rft.issue=6&rft.spage=1405&rft.epage=1411&rft.pages=1405-1411&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202301142&rft_dat=%3Cproquest_cross%3E2998629319%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=2998629319&rft_id=info:pmid/&rfr_iscdi=true