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...
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Veröffentlicht in: | Advanced synthesis & catalysis 2024-03, Vol.366 (6), p.1405-1411 |
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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 |
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Moreover, this protocol is applied to the synthesis of drug molecules Propipocaine and Proroxan. 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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 & 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 & 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. 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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 |
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