Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor
The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N‐aryl and N‐alkyl amines, but also provides new insigh...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2016-08, Vol.55 (33), p.9615-9619 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 9619 |
|---|---|
| container_issue | 33 |
| container_start_page | 9615 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 55 |
| creator | Pan, Hui-Jie Zhang, Yao Shan, Chunhui Yu, Zhaoyuan Lan, Yu Zhao, Yu |
| description | The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N‐aryl and N‐alkyl amines, but also provides new insight into the mechanism of the ATH of imines. Both experimental and computational studies provide support for the reaction pathway involving an iridium alkoxide as the reducing species.
The influence of alcohol, as the hydrogen donor, on the efficiency and enantioselectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported. This discovery not only leads to a highly enantioselective access to N‐aryl as well as N‐alkyl chiral amines, but also provides new insight into the mechanism of iridium‐catalyzed ATH of imines using alcohol. |
| doi_str_mv | 10.1002/anie.201604025 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1809051305</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>4143623631</sourcerecordid><originalsourceid>FETCH-LOGICAL-c6125-bcf127c66128acf04c1d945928a3ce98edeb96f616c06486d3d5eda664d186303</originalsourceid><addsrcrecordid>eNqFkUFv0zAYhi0EYmNw5YgsceGSYsexk3Crtq6rNI0DhUpcLNf-vHkk9mYnjPDrcdVRIQ5w8vfJz_vI8ovQa0pmlJDyvfIOZiWhglSk5E_QMeUlLVhds6d5rhgr6obTI_QipdvMNw0Rz9FRWbO6yvMx-jlPU9_DEJ3G66h8shDxxWRiuAavBhc8Dhaveuch4TE5f43nnQ43ofuAF9Y67cDrCStv8CfoQA_uuxvyHgGvvO3GfAsGbyc83MDBi8-CD_ElemZVl-DV43mCPp8v1qcXxeXH5ep0flloQUtebLWlZa1FXhqlLak0NW3F27wxDW0DBratsIIKTUTVCMMMB6OEqAxtBCPsBL3be-9iuB8hDbJ3SUPXKQ9hTJI2pCWcMsIz-vYv9DaM0efXSdqK_JO8Zu0_qYZmDWVs55rtKR1DShGsvIuuV3GSlMhdd3LXnTx0lwNvHrXjtgdzwH-XlYF2Dzy4Dqb_6OT8arX4U17ssy4N8OOQVfGbFNnP5eZqKb9szjbLdf1V1uwXZDC0iw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1810531335</pqid></control><display><type>article</type><title>Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor</title><source>Wiley Journals</source><creator>Pan, Hui-Jie ; Zhang, Yao ; Shan, Chunhui ; Yu, Zhaoyuan ; Lan, Yu ; Zhao, Yu</creator><creatorcontrib>Pan, Hui-Jie ; Zhang, Yao ; Shan, Chunhui ; Yu, Zhaoyuan ; Lan, Yu ; Zhao, Yu</creatorcontrib><description>The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N‐aryl and N‐alkyl amines, but also provides new insight into the mechanism of the ATH of imines. Both experimental and computational studies provide support for the reaction pathway involving an iridium alkoxide as the reducing species.
The influence of alcohol, as the hydrogen donor, on the efficiency and enantioselectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported. This discovery not only leads to a highly enantioselective access to N‐aryl as well as N‐alkyl chiral amines, but also provides new insight into the mechanism of iridium‐catalyzed ATH of imines using alcohol.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201604025</identifier><identifier>PMID: 27374880</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Alcohol ; Alcohols ; Amines ; Aromatic compounds ; Computer applications ; cooperative effects ; Efficiency ; Enantiomers ; enantioselectivity ; Hydrogen storage ; Hydrogenation ; Imines ; Iridium ; Selectivity</subject><ispartof>Angewandte Chemie International Edition, 2016-08, Vol.55 (33), p.9615-9619</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6125-bcf127c66128acf04c1d945928a3ce98edeb96f616c06486d3d5eda664d186303</citedby><cites>FETCH-LOGICAL-c6125-bcf127c66128acf04c1d945928a3ce98edeb96f616c06486d3d5eda664d186303</cites><orcidid>0000-0002-2944-1315</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.201604025$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201604025$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27374880$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pan, Hui-Jie</creatorcontrib><creatorcontrib>Zhang, Yao</creatorcontrib><creatorcontrib>Shan, Chunhui</creatorcontrib><creatorcontrib>Yu, Zhaoyuan</creatorcontrib><creatorcontrib>Lan, Yu</creatorcontrib><creatorcontrib>Zhao, Yu</creatorcontrib><title>Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N‐aryl and N‐alkyl amines, but also provides new insight into the mechanism of the ATH of imines. Both experimental and computational studies provide support for the reaction pathway involving an iridium alkoxide as the reducing species.
The influence of alcohol, as the hydrogen donor, on the efficiency and enantioselectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported. This discovery not only leads to a highly enantioselective access to N‐aryl as well as N‐alkyl chiral amines, but also provides new insight into the mechanism of iridium‐catalyzed ATH of imines using alcohol.</description><subject>Alcohol</subject><subject>Alcohols</subject><subject>Amines</subject><subject>Aromatic compounds</subject><subject>Computer applications</subject><subject>cooperative effects</subject><subject>Efficiency</subject><subject>Enantiomers</subject><subject>enantioselectivity</subject><subject>Hydrogen storage</subject><subject>Hydrogenation</subject><subject>Imines</subject><subject>Iridium</subject><subject>Selectivity</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkUFv0zAYhi0EYmNw5YgsceGSYsexk3Crtq6rNI0DhUpcLNf-vHkk9mYnjPDrcdVRIQ5w8vfJz_vI8ovQa0pmlJDyvfIOZiWhglSk5E_QMeUlLVhds6d5rhgr6obTI_QipdvMNw0Rz9FRWbO6yvMx-jlPU9_DEJ3G66h8shDxxWRiuAavBhc8Dhaveuch4TE5f43nnQ43ofuAF9Y67cDrCStv8CfoQA_uuxvyHgGvvO3GfAsGbyc83MDBi8-CD_ElemZVl-DV43mCPp8v1qcXxeXH5ep0flloQUtebLWlZa1FXhqlLak0NW3F27wxDW0DBratsIIKTUTVCMMMB6OEqAxtBCPsBL3be-9iuB8hDbJ3SUPXKQ9hTJI2pCWcMsIz-vYv9DaM0efXSdqK_JO8Zu0_qYZmDWVs55rtKR1DShGsvIuuV3GSlMhdd3LXnTx0lwNvHrXjtgdzwH-XlYF2Dzy4Dqb_6OT8arX4U17ssy4N8OOQVfGbFNnP5eZqKb9szjbLdf1V1uwXZDC0iw</recordid><startdate>20160808</startdate><enddate>20160808</enddate><creator>Pan, Hui-Jie</creator><creator>Zhang, Yao</creator><creator>Shan, Chunhui</creator><creator>Yu, Zhaoyuan</creator><creator>Lan, Yu</creator><creator>Zhao, Yu</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2944-1315</orcidid></search><sort><creationdate>20160808</creationdate><title>Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor</title><author>Pan, Hui-Jie ; Zhang, Yao ; Shan, Chunhui ; Yu, Zhaoyuan ; Lan, Yu ; Zhao, Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6125-bcf127c66128acf04c1d945928a3ce98edeb96f616c06486d3d5eda664d186303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Alcohol</topic><topic>Alcohols</topic><topic>Amines</topic><topic>Aromatic compounds</topic><topic>Computer applications</topic><topic>cooperative effects</topic><topic>Efficiency</topic><topic>Enantiomers</topic><topic>enantioselectivity</topic><topic>Hydrogen storage</topic><topic>Hydrogenation</topic><topic>Imines</topic><topic>Iridium</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pan, Hui-Jie</creatorcontrib><creatorcontrib>Zhang, Yao</creatorcontrib><creatorcontrib>Shan, Chunhui</creatorcontrib><creatorcontrib>Yu, Zhaoyuan</creatorcontrib><creatorcontrib>Lan, Yu</creatorcontrib><creatorcontrib>Zhao, Yu</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><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>Pan, Hui-Jie</au><au>Zhang, Yao</au><au>Shan, Chunhui</au><au>Yu, Zhaoyuan</au><au>Lan, Yu</au><au>Zhao, Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-08-08</date><risdate>2016</risdate><volume>55</volume><issue>33</issue><spage>9615</spage><epage>9619</epage><pages>9615-9619</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N‐aryl and N‐alkyl amines, but also provides new insight into the mechanism of the ATH of imines. Both experimental and computational studies provide support for the reaction pathway involving an iridium alkoxide as the reducing species.
The influence of alcohol, as the hydrogen donor, on the efficiency and enantioselectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported. This discovery not only leads to a highly enantioselective access to N‐aryl as well as N‐alkyl chiral amines, but also provides new insight into the mechanism of iridium‐catalyzed ATH of imines using alcohol.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27374880</pmid><doi>10.1002/anie.201604025</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-2944-1315</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2016-08, Vol.55 (33), p.9615-9619 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1809051305 |
| source | Wiley Journals |
| subjects | Alcohol Alcohols Amines Aromatic compounds Computer applications cooperative effects Efficiency Enantiomers enantioselectivity Hydrogen storage Hydrogenation Imines Iridium Selectivity |
| title | Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T04%3A32%3A24IST&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=Asymmetric%20Transfer%20Hydrogenation%20of%20Imines%20using%20Alcohol:%20Efficiency%20and%20Selectivity%20are%20Influenced%20by%20the%20Hydrogen%20Donor&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Pan,%20Hui-Jie&rft.date=2016-08-08&rft.volume=55&rft.issue=33&rft.spage=9615&rft.epage=9619&rft.pages=9615-9619&rft.issn=1433-7851&rft.eissn=1521-3773&rft.coden=ACIEAY&rft_id=info:doi/10.1002/anie.201604025&rft_dat=%3Cproquest_cross%3E4143623631%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=1810531335&rft_id=info:pmid/27374880&rfr_iscdi=true |