Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives
An efficient rhodium‐catalyzed asymmetric hydrogenation of challenging tetrasubstituted cyclic enamides has been developed, affording cyclic chiral amides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise sy...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2017-02, Vol.359 (4), p.597-602 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 602 |
|---|---|
| container_issue | 4 |
| container_start_page | 597 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 359 |
| creator | Li, Xiuxiu You, Cai Yang, Hailong Che, Jinteng Chen, Pengyu Yang, Yusheng Lv, Hui Zhang, Xumu |
| description | An efficient rhodium‐catalyzed asymmetric hydrogenation of challenging tetrasubstituted cyclic enamides has been developed, affording cyclic chiral amides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise synthetic route to chiral cycloalkylamines with two contiguous stereogenic centers. The potential utility of this protocol in the synthesis of bioactive molecules is also disclosed. |
| doi_str_mv | 10.1002/adsc.201601135 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1884100339</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1920417566</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3875-7de796efa416378817fec285cad4b2077675a5b4eedee808f6489197b19086563</originalsourceid><addsrcrecordid>eNqFkT1v2zAQhoWiAZo6XTsTyJLFDimJH8pmyM4HYCBAms4ETZ0appTokpQDdeqYMb8xvyR0HSRAl053ODzvi7t7s-wrwTOCcX6qmqBnOSYME1LQD9khYYROS8Kqj289xZ-yzyHcY0y44Pwwe7y5c40Zuuc_T7WKyo6_oUHzMHYdRG80uhwb735Ar6JxPXItuk1zFYZ1iCYOMcH1qG0Cl73qTAPhDC3b1mgDfURzrSEEFB2q74xX9i_rlP052gT3gBbgzTZZbyEcZQetsgG-vNZJ9v18eVtfTlfXF1f1fDXVheB0yhvgFYNWpbsKLgThLehcUK2acp1jzhmniq5LgAZAYNGyUlSk4mtSYcEoKybZyd53492vAUKUnQkarFU9uCFIIkSZ3lkUVUKP_0Hv3eD7tJ0kVY5LwinbGc72lPYuBA-t3HjTKT9KguUuGLkLRr4FkwTVXvBgLIz_oeV88a1-174ANqOUvA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1920417566</pqid></control><display><type>article</type><title>Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives</title><source>Wiley Online Library All Journals</source><creator>Li, Xiuxiu ; You, Cai ; Yang, Hailong ; Che, Jinteng ; Chen, Pengyu ; Yang, Yusheng ; Lv, Hui ; Zhang, Xumu</creator><creatorcontrib>Li, Xiuxiu ; You, Cai ; Yang, Hailong ; Che, Jinteng ; Chen, Pengyu ; Yang, Yusheng ; Lv, Hui ; Zhang, Xumu</creatorcontrib><description>An efficient rhodium‐catalyzed asymmetric hydrogenation of challenging tetrasubstituted cyclic enamides has been developed, affording cyclic chiral amides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise synthetic route to chiral cycloalkylamines with two contiguous stereogenic centers. The potential utility of this protocol in the synthesis of bioactive molecules is also disclosed.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201601135</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Amides ; amines ; asymmetric synthesis ; Asymmetry ; Biocompatibility ; Biomedical materials ; Catalysis ; Chemical synthesis ; Derivatives ; enantioselectivity ; Hydrogenation ; Rhodium ; Surgical implants ; Synthesis (chemistry) ; Utilities</subject><ispartof>Advanced synthesis & catalysis, 2017-02, Vol.359 (4), p.597-602</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3875-7de796efa416378817fec285cad4b2077675a5b4eedee808f6489197b19086563</citedby><cites>FETCH-LOGICAL-c3875-7de796efa416378817fec285cad4b2077675a5b4eedee808f6489197b19086563</cites></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.201601135$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201601135$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Li, Xiuxiu</creatorcontrib><creatorcontrib>You, Cai</creatorcontrib><creatorcontrib>Yang, Hailong</creatorcontrib><creatorcontrib>Che, Jinteng</creatorcontrib><creatorcontrib>Chen, Pengyu</creatorcontrib><creatorcontrib>Yang, Yusheng</creatorcontrib><creatorcontrib>Lv, Hui</creatorcontrib><creatorcontrib>Zhang, Xumu</creatorcontrib><title>Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives</title><title>Advanced synthesis & catalysis</title><description>An efficient rhodium‐catalyzed asymmetric hydrogenation of challenging tetrasubstituted cyclic enamides has been developed, affording cyclic chiral amides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise synthetic route to chiral cycloalkylamines with two contiguous stereogenic centers. The potential utility of this protocol in the synthesis of bioactive molecules is also disclosed.</description><subject>Amides</subject><subject>amines</subject><subject>asymmetric synthesis</subject><subject>Asymmetry</subject><subject>Biocompatibility</subject><subject>Biomedical materials</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Derivatives</subject><subject>enantioselectivity</subject><subject>Hydrogenation</subject><subject>Rhodium</subject><subject>Surgical implants</subject><subject>Synthesis (chemistry)</subject><subject>Utilities</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkT1v2zAQhoWiAZo6XTsTyJLFDimJH8pmyM4HYCBAms4ETZ0appTokpQDdeqYMb8xvyR0HSRAl053ODzvi7t7s-wrwTOCcX6qmqBnOSYME1LQD9khYYROS8Kqj289xZ-yzyHcY0y44Pwwe7y5c40Zuuc_T7WKyo6_oUHzMHYdRG80uhwb735Ar6JxPXItuk1zFYZ1iCYOMcH1qG0Cl73qTAPhDC3b1mgDfURzrSEEFB2q74xX9i_rlP052gT3gBbgzTZZbyEcZQetsgG-vNZJ9v18eVtfTlfXF1f1fDXVheB0yhvgFYNWpbsKLgThLehcUK2acp1jzhmniq5LgAZAYNGyUlSk4mtSYcEoKybZyd53492vAUKUnQkarFU9uCFIIkSZ3lkUVUKP_0Hv3eD7tJ0kVY5LwinbGc72lPYuBA-t3HjTKT9KguUuGLkLRr4FkwTVXvBgLIz_oeV88a1-174ANqOUvA</recordid><startdate>20170220</startdate><enddate>20170220</enddate><creator>Li, Xiuxiu</creator><creator>You, Cai</creator><creator>Yang, Hailong</creator><creator>Che, Jinteng</creator><creator>Chen, Pengyu</creator><creator>Yang, Yusheng</creator><creator>Lv, Hui</creator><creator>Zhang, Xumu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20170220</creationdate><title>Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives</title><author>Li, Xiuxiu ; You, Cai ; Yang, Hailong ; Che, Jinteng ; Chen, Pengyu ; Yang, Yusheng ; Lv, Hui ; Zhang, Xumu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3875-7de796efa416378817fec285cad4b2077675a5b4eedee808f6489197b19086563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Amides</topic><topic>amines</topic><topic>asymmetric synthesis</topic><topic>Asymmetry</topic><topic>Biocompatibility</topic><topic>Biomedical materials</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Derivatives</topic><topic>enantioselectivity</topic><topic>Hydrogenation</topic><topic>Rhodium</topic><topic>Surgical implants</topic><topic>Synthesis (chemistry)</topic><topic>Utilities</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Xiuxiu</creatorcontrib><creatorcontrib>You, Cai</creatorcontrib><creatorcontrib>Yang, Hailong</creatorcontrib><creatorcontrib>Che, Jinteng</creatorcontrib><creatorcontrib>Chen, Pengyu</creatorcontrib><creatorcontrib>Yang, Yusheng</creatorcontrib><creatorcontrib>Lv, Hui</creatorcontrib><creatorcontrib>Zhang, Xumu</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>Li, Xiuxiu</au><au>You, Cai</au><au>Yang, Hailong</au><au>Che, Jinteng</au><au>Chen, Pengyu</au><au>Yang, Yusheng</au><au>Lv, Hui</au><au>Zhang, Xumu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2017-02-20</date><risdate>2017</risdate><volume>359</volume><issue>4</issue><spage>597</spage><epage>602</epage><pages>597-602</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An efficient rhodium‐catalyzed asymmetric hydrogenation of challenging tetrasubstituted cyclic enamides has been developed, affording cyclic chiral amides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise synthetic route to chiral cycloalkylamines with two contiguous stereogenic centers. The potential utility of this protocol in the synthesis of bioactive molecules is also disclosed.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201601135</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2017-02, Vol.359 (4), p.597-602 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1884100339 |
| source | Wiley Online Library All Journals |
| subjects | Amides amines asymmetric synthesis Asymmetry Biocompatibility Biomedical materials Catalysis Chemical synthesis Derivatives enantioselectivity Hydrogenation Rhodium Surgical implants Synthesis (chemistry) Utilities |
| title | Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T10%3A41%3A39IST&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=Rhodium%E2%80%90Catalyzed%20Asymmetric%20Hydrogenation%20of%20Tetrasubstituted%20Cyclic%20Enamides:%20Efficient%20Access%20to%20Chiral%20Cycloalkylamine%20Derivatives&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Li,%20Xiuxiu&rft.date=2017-02-20&rft.volume=359&rft.issue=4&rft.spage=597&rft.epage=602&rft.pages=597-602&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201601135&rft_dat=%3Cproquest_cross%3E1920417566%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=1920417566&rft_id=info:pmid/&rfr_iscdi=true |