Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered b...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-03, Vol.59 (13), p.5321-5325 |
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| creator | Hu, Le' an Zhang, Yao Zhang, Qing‐Wen Yin, Qin Zhang, Xumu |
| description | A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group.
OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity. |
| doi_str_mv | 10.1002/anie.201915459 |
| format | Article |
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OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201915459</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Amination ; amines ; Ammonium ; Ammonium salts ; Asymmetry ; Bioactive compounds ; diaryl ketones ; homogeneous catalysis ; Ketones ; reductive amination ; Ruthenium ; Salts</subject><ispartof>Angewandte Chemie International Edition, 2020-03, Vol.59 (13), p.5321-5325</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-3534-3786</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%2Fanie.201915459$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201915459$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Hu, Le' an</creatorcontrib><creatorcontrib>Zhang, Yao</creatorcontrib><creatorcontrib>Zhang, Qing‐Wen</creatorcontrib><creatorcontrib>Yin, Qin</creatorcontrib><creatorcontrib>Zhang, Xumu</creatorcontrib><title>Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2</title><title>Angewandte Chemie International Edition</title><description>A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group.
OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity.</description><subject>Amination</subject><subject>amines</subject><subject>Ammonium</subject><subject>Ammonium salts</subject><subject>Asymmetry</subject><subject>Bioactive compounds</subject><subject>diaryl ketones</subject><subject>homogeneous catalysis</subject><subject>Ketones</subject><subject>reductive amination</subject><subject>Ruthenium</subject><subject>Salts</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkbtOxDAQRSMEErDQUluioQn4kcROuVoei0AgLVBHQzIGI8eB2GEVKj6Bb-RL8AKioJoZ6czr3iTZY_SQUcqPwBk85JSVLM_yci3ZYjlnqZBSrMc8EyKVKmebybb3T5FXihZbyftiCI_ozNB-vn_MIIAd37Ahx6bHOpCpH9sWQ29qssBmqIN5RTJtjYNgOkc6HUHoR0vANeQmYATB2pHMjWuwj3MuMHQOPVma8Bgb2261idyADf67Z853kg0N1uPub5wkd6cnt7N5enl9dj6bXqYPnKkyFRpkU2uus5pJrRSjAiArJVDQ90rpAnOlkWuJTNQFy7UUsi5AAQelIT4_SQ5-5j733cuAPlSt8TVaCw67wVdcZKzgtPxG9_-hT93Qu3hdpKTkUV61osofamksjtVzb9ooRcVotXKjWrlR_blRTa_OT_4q8QWFtIMT</recordid><startdate>20200323</startdate><enddate>20200323</enddate><creator>Hu, Le' an</creator><creator>Zhang, Yao</creator><creator>Zhang, Qing‐Wen</creator><creator>Yin, Qin</creator><creator>Zhang, Xumu</creator><general>Wiley Subscription Services, Inc</general><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3534-3786</orcidid></search><sort><creationdate>20200323</creationdate><title>Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2</title><author>Hu, Le' an ; Zhang, Yao ; Zhang, Qing‐Wen ; Yin, Qin ; Zhang, Xumu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g2189-3fa7dcf2f4c17f88103aa497a0afb88f6e58fe2f7e13c615f737c6a8a2a8fa433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amination</topic><topic>amines</topic><topic>Ammonium</topic><topic>Ammonium salts</topic><topic>Asymmetry</topic><topic>Bioactive compounds</topic><topic>diaryl ketones</topic><topic>homogeneous catalysis</topic><topic>Ketones</topic><topic>reductive amination</topic><topic>Ruthenium</topic><topic>Salts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Le' an</creatorcontrib><creatorcontrib>Zhang, Yao</creatorcontrib><creatorcontrib>Zhang, Qing‐Wen</creatorcontrib><creatorcontrib>Yin, Qin</creatorcontrib><creatorcontrib>Zhang, Xumu</creatorcontrib><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Le' an</au><au>Zhang, Yao</au><au>Zhang, Qing‐Wen</au><au>Yin, Qin</au><au>Zhang, Xumu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2020-03-23</date><risdate>2020</risdate><volume>59</volume><issue>13</issue><spage>5321</spage><epage>5325</epage><pages>5321-5325</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group.
OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.201915459</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-3534-3786</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Amination amines Ammonium Ammonium salts Asymmetry Bioactive compounds diaryl ketones homogeneous catalysis Ketones reductive amination Ruthenium Salts |
| title | Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2 |
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