Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement
A sweet dysprosition: A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols into 4‐aminocyclopentenones by a 4π electrocyclization has been developed. The aza‐Piancatelli rearrangement affords a single trans diastereomer from both aryl‐ and alkyl‐substituted furylcarb...
Gespeichert in:
Veröffentlicht in: | Angewandte Chemie (International ed.) 2010-12, Vol.49 (49), p.9484-9487 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 9487 |
---|---|
container_issue | 49 |
container_start_page | 9484 |
container_title | Angewandte Chemie (International ed.) |
container_volume | 49 |
creator | Veits, Gesine K Wenz, Donald R Read de Alaniz, Javier |
description | A sweet dysprosition: A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols into 4‐aminocyclopentenones by a 4π electrocyclization has been developed. The aza‐Piancatelli rearrangement affords a single trans diastereomer from both aryl‐ and alkyl‐substituted furylcarbinols. |
doi_str_mv | 10.1002/anie.201005131 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_815960749</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>815960749</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4721-e745c479c2a37613ea4656886b12da80f1d73924cc0e2d1ea2cea2c46e11a3c93</originalsourceid><addsrcrecordid>eNqFkM1v1DAQxS0EoqVw5Qi-AYcs_kjihNtqKSWolKrdUsTFmjqT1pA4i51Vmx76t9erlBU3ZFnzNPrN08wj5CVnM86YeA_O4kywqDMu-SOyyzPBE6mUfBx1KmWiiozvkGch_Ip8UbD8KdkRnGVSSL5L7r6jDzDYFulXHK76mja9p8MV0tPRxRJsoH1D02TeWdeb0bT9Ct2ArncYPtCPY1j5Pth197aqqnd06W3TwoB0AQO04y3WdH4LybEFZ2K7bS09QfAe3CV20ec5edJAG_DFQ90jZ5_2l4vPyeG3g2oxP0xMquI9qNIsqtIIkCrnEiHNs7wo8gsuaihYw2slS5Eaw1DUHEGYzU9z5BykKeUeeTP5xm3_rDEMurPBxH3AYb8OuuBZmTOVbsjZRJp4V_DY6JW3HfhRc6Y3ketN5HobeRx49WC9vuiw3uJ_M45AOQHXMeXxP3Z6flTt_2ueTLM2DHiznQX_W-dKqkyfHx3o5fnJ8Q-x-KJ_Rv71xDfQa7j0Nuiz02gnGS_jixvdAxDSpzA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>815960749</pqid></control><display><type>article</type><title>Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Veits, Gesine K ; Wenz, Donald R ; Read de Alaniz, Javier</creator><creatorcontrib>Veits, Gesine K ; Wenz, Donald R ; Read de Alaniz, Javier</creatorcontrib><description>A sweet dysprosition: A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols into 4‐aminocyclopentenones by a 4π electrocyclization has been developed. The aza‐Piancatelli rearrangement affords a single trans diastereomer from both aryl‐ and alkyl‐substituted furylcarbinols.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201005131</identifier><identifier>PMID: 21053231</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>Catalysis ; cyclization ; Cyclopentanes - chemical synthesis ; Cyclopentanes - chemistry ; domino reactions ; dysprosium ; Dysprosium - chemistry ; Furans - chemistry ; lanthanides ; Mesylates - chemistry ; Molecular Structure ; rearrangement ; Stereoisomerism</subject><ispartof>Angewandte Chemie (International ed.), 2010-12, Vol.49 (49), p.9484-9487</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4721-e745c479c2a37613ea4656886b12da80f1d73924cc0e2d1ea2cea2c46e11a3c93</citedby><cites>FETCH-LOGICAL-c4721-e745c479c2a37613ea4656886b12da80f1d73924cc0e2d1ea2cea2c46e11a3c93</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%2Fanie.201005131$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201005131$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21053231$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Veits, Gesine K</creatorcontrib><creatorcontrib>Wenz, Donald R</creatorcontrib><creatorcontrib>Read de Alaniz, Javier</creatorcontrib><title>Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement</title><title>Angewandte Chemie (International ed.)</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A sweet dysprosition: A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols into 4‐aminocyclopentenones by a 4π electrocyclization has been developed. The aza‐Piancatelli rearrangement affords a single trans diastereomer from both aryl‐ and alkyl‐substituted furylcarbinols.</description><subject>Catalysis</subject><subject>cyclization</subject><subject>Cyclopentanes - chemical synthesis</subject><subject>Cyclopentanes - chemistry</subject><subject>domino reactions</subject><subject>dysprosium</subject><subject>Dysprosium - chemistry</subject><subject>Furans - chemistry</subject><subject>lanthanides</subject><subject>Mesylates - chemistry</subject><subject>Molecular Structure</subject><subject>rearrangement</subject><subject>Stereoisomerism</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1v1DAQxS0EoqVw5Qi-AYcs_kjihNtqKSWolKrdUsTFmjqT1pA4i51Vmx76t9erlBU3ZFnzNPrN08wj5CVnM86YeA_O4kywqDMu-SOyyzPBE6mUfBx1KmWiiozvkGch_Ip8UbD8KdkRnGVSSL5L7r6jDzDYFulXHK76mja9p8MV0tPRxRJsoH1D02TeWdeb0bT9Ct2ArncYPtCPY1j5Pth197aqqnd06W3TwoB0AQO04y3WdH4LybEFZ2K7bS09QfAe3CV20ec5edJAG_DFQ90jZ5_2l4vPyeG3g2oxP0xMquI9qNIsqtIIkCrnEiHNs7wo8gsuaihYw2slS5Eaw1DUHEGYzU9z5BykKeUeeTP5xm3_rDEMurPBxH3AYb8OuuBZmTOVbsjZRJp4V_DY6JW3HfhRc6Y3ketN5HobeRx49WC9vuiw3uJ_M45AOQHXMeXxP3Z6flTt_2ueTLM2DHiznQX_W-dKqkyfHx3o5fnJ8Q-x-KJ_Rv71xDfQa7j0Nuiz02gnGS_jixvdAxDSpzA</recordid><startdate>20101203</startdate><enddate>20101203</enddate><creator>Veits, Gesine K</creator><creator>Wenz, Donald R</creator><creator>Read de Alaniz, Javier</creator><general>Wiley-VCH Verlag</general><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20101203</creationdate><title>Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement</title><author>Veits, Gesine K ; Wenz, Donald R ; Read de Alaniz, Javier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4721-e745c479c2a37613ea4656886b12da80f1d73924cc0e2d1ea2cea2c46e11a3c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Catalysis</topic><topic>cyclization</topic><topic>Cyclopentanes - chemical synthesis</topic><topic>Cyclopentanes - chemistry</topic><topic>domino reactions</topic><topic>dysprosium</topic><topic>Dysprosium - chemistry</topic><topic>Furans - chemistry</topic><topic>lanthanides</topic><topic>Mesylates - chemistry</topic><topic>Molecular Structure</topic><topic>rearrangement</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Veits, Gesine K</creatorcontrib><creatorcontrib>Wenz, Donald R</creatorcontrib><creatorcontrib>Read de Alaniz, Javier</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Veits, Gesine K</au><au>Wenz, Donald R</au><au>Read de Alaniz, Javier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2010-12-03</date><risdate>2010</risdate><volume>49</volume><issue>49</issue><spage>9484</spage><epage>9487</epage><pages>9484-9487</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A sweet dysprosition: A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols into 4‐aminocyclopentenones by a 4π electrocyclization has been developed. The aza‐Piancatelli rearrangement affords a single trans diastereomer from both aryl‐ and alkyl‐substituted furylcarbinols.</abstract><cop>Weinheim</cop><pub>Wiley-VCH Verlag</pub><pmid>21053231</pmid><doi>10.1002/anie.201005131</doi><tpages>4</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1433-7851 |
ispartof | Angewandte Chemie (International ed.), 2010-12, Vol.49 (49), p.9484-9487 |
issn | 1433-7851 1521-3773 |
language | eng |
recordid | cdi_proquest_miscellaneous_815960749 |
source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
subjects | Catalysis cyclization Cyclopentanes - chemical synthesis Cyclopentanes - chemistry domino reactions dysprosium Dysprosium - chemistry Furans - chemistry lanthanides Mesylates - chemistry Molecular Structure rearrangement Stereoisomerism |
title | Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T03%3A42%3A57IST&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=Versatile%20Method%20for%20the%20Synthesis%20of%204-Aminocyclopentenones:%20Dysprosium(III)%20Triflate%20Catalyzed%20Aza-Piancatelli%20Rearrangement&rft.jtitle=Angewandte%20Chemie%20(International%20ed.)&rft.au=Veits,%20Gesine%20K&rft.date=2010-12-03&rft.volume=49&rft.issue=49&rft.spage=9484&rft.epage=9487&rft.pages=9484-9487&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201005131&rft_dat=%3Cproquest_cross%3E815960749%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=815960749&rft_id=info:pmid/21053231&rfr_iscdi=true |