Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams

'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2011-10, Vol.50 (42), p.9884-9887
Hauptverfasser: Ichinose, Masami, Suematsu, Hidehiro, Yasutomi, Yoichi, Nishioka, Yota, Uchida, Tatsuya, Katsuki, Tsutomu
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 9887
container_issue 42
container_start_page 9884
container_title Angewandte Chemie International Edition
container_volume 50
creator Ichinose, Masami
Suematsu, Hidehiro
Yasutomi, Yoichi
Nishioka, Yota
Uchida, Tatsuya
Katsuki, Tsutomu
description 'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron‐donating group.
doi_str_mv 10.1002/anie.201101801
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1093478905</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1093478905</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4491-fe7fa6e26d4b2b27797e02291704cd6b2b872587f6e773e094398f413f3f4a403</originalsourceid><addsrcrecordid>eNqFkMtu1DAUhiNERS-wZYm8ZJPBt8Q2u-kwbaeq2gVFZWd5MsfC4DjT2KENr8OD8Ei8Ah6ljNixOj7W93_S-YviNcEzgjF9Z4KDGcWEYCIxeVYckYqSkgnBnuc3Z6wUsiKHxXGMXzMvJa5fFIeUKMKoFEdFXAYTkusieGiS-w5oFVJv2i6vgzc9OoXwY_SuQYvfP39doNMubNC8dcHkUHiPlta6xkFI6OMY0heILqLOopttco3xfkTzybrTdHHwybTxZXFgjY_w6mmeFJ_OlreLi_Lq5ny1mF-VDeeKlBaENTXQesPXdE2FUAIwpYoIzJtNnf-koJUUtoZ8LmDFmZKWE2aZ5YZjdlK8nbzbvrsfICbdutiA9yZAN0RNsGJcSIWrjM4mtOm7GHuwetu71vRjhvSuaL0rWu-LzoE3T-5h3cJmj_9tNgNqAh6ch_E_Oj2_Xi3_lZdT1sUEj_us6b_pWjBR6bvrc315-4GR6vNC37E_fXSbOQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1093478905</pqid></control><display><type>article</type><title>Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Ichinose, Masami ; Suematsu, Hidehiro ; Yasutomi, Yoichi ; Nishioka, Yota ; Uchida, Tatsuya ; Katsuki, Tsutomu</creator><creatorcontrib>Ichinose, Masami ; Suematsu, Hidehiro ; Yasutomi, Yoichi ; Nishioka, Yota ; Uchida, Tatsuya ; Katsuki, Tsutomu</creatorcontrib><description>'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron‐donating group.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201101801</identifier><identifier>PMID: 21913287</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amination ; CH amination ; heterocycles ; homogeneous catalysis ; iridium ; Molecular Structure ; Optical Phenomena ; Stereoisomerism ; Sulfonamides - chemical synthesis ; Sulfonamides - chemistry ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2011-10, Vol.50 (42), p.9884-9887</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4491-fe7fa6e26d4b2b27797e02291704cd6b2b872587f6e773e094398f413f3f4a403</citedby><cites>FETCH-LOGICAL-c4491-fe7fa6e26d4b2b27797e02291704cd6b2b872587f6e773e094398f413f3f4a403</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.201101801$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201101801$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21913287$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ichinose, Masami</creatorcontrib><creatorcontrib>Suematsu, Hidehiro</creatorcontrib><creatorcontrib>Yasutomi, Yoichi</creatorcontrib><creatorcontrib>Nishioka, Yota</creatorcontrib><creatorcontrib>Uchida, Tatsuya</creatorcontrib><creatorcontrib>Katsuki, Tsutomu</creatorcontrib><title>Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron‐donating group.</description><subject>Amination</subject><subject>CH amination</subject><subject>heterocycles</subject><subject>homogeneous catalysis</subject><subject>iridium</subject><subject>Molecular Structure</subject><subject>Optical Phenomena</subject><subject>Stereoisomerism</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - chemistry</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtu1DAUhiNERS-wZYm8ZJPBt8Q2u-kwbaeq2gVFZWd5MsfC4DjT2KENr8OD8Ei8Ah6ljNixOj7W93_S-YviNcEzgjF9Z4KDGcWEYCIxeVYckYqSkgnBnuc3Z6wUsiKHxXGMXzMvJa5fFIeUKMKoFEdFXAYTkusieGiS-w5oFVJv2i6vgzc9OoXwY_SuQYvfP39doNMubNC8dcHkUHiPlta6xkFI6OMY0heILqLOopttco3xfkTzybrTdHHwybTxZXFgjY_w6mmeFJ_OlreLi_Lq5ny1mF-VDeeKlBaENTXQesPXdE2FUAIwpYoIzJtNnf-koJUUtoZ8LmDFmZKWE2aZ5YZjdlK8nbzbvrsfICbdutiA9yZAN0RNsGJcSIWrjM4mtOm7GHuwetu71vRjhvSuaL0rWu-LzoE3T-5h3cJmj_9tNgNqAh6ch_E_Oj2_Xi3_lZdT1sUEj_us6b_pWjBR6bvrc315-4GR6vNC37E_fXSbOQ</recordid><startdate>20111010</startdate><enddate>20111010</enddate><creator>Ichinose, Masami</creator><creator>Suematsu, Hidehiro</creator><creator>Yasutomi, Yoichi</creator><creator>Nishioka, Yota</creator><creator>Uchida, Tatsuya</creator><creator>Katsuki, Tsutomu</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><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>20111010</creationdate><title>Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams</title><author>Ichinose, Masami ; Suematsu, Hidehiro ; Yasutomi, Yoichi ; Nishioka, Yota ; Uchida, Tatsuya ; Katsuki, Tsutomu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4491-fe7fa6e26d4b2b27797e02291704cd6b2b872587f6e773e094398f413f3f4a403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Amination</topic><topic>CH amination</topic><topic>heterocycles</topic><topic>homogeneous catalysis</topic><topic>iridium</topic><topic>Molecular Structure</topic><topic>Optical Phenomena</topic><topic>Stereoisomerism</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - chemistry</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ichinose, Masami</creatorcontrib><creatorcontrib>Suematsu, Hidehiro</creatorcontrib><creatorcontrib>Yasutomi, Yoichi</creatorcontrib><creatorcontrib>Nishioka, Yota</creatorcontrib><creatorcontrib>Uchida, Tatsuya</creatorcontrib><creatorcontrib>Katsuki, Tsutomu</creatorcontrib><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 Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ichinose, Masami</au><au>Suematsu, Hidehiro</au><au>Yasutomi, Yoichi</au><au>Nishioka, Yota</au><au>Uchida, Tatsuya</au><au>Katsuki, Tsutomu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2011-10-10</date><risdate>2011</risdate><volume>50</volume><issue>42</issue><spage>9884</spage><epage>9887</epage><pages>9884-9887</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>'Salen' along: The iridium(III)–salen complex 1 efficiently catalyzes the title reaction of 2‐ethylbenzenesulfonyl azides to give five‐membered sultams with high enantioselectivity. Other 2‐alkyl‐substitued substrates lead to five‐ and six‐membered sultams with high enantioselectivity; the regioselectivity depends upon the substrate and the catalyst used. EDG=electron‐donating group.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21913287</pmid><doi>10.1002/anie.201101801</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2011-10, Vol.50 (42), p.9884-9887
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_1093478905
source MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects Amination
CH amination
heterocycles
homogeneous catalysis
iridium
Molecular Structure
Optical Phenomena
Stereoisomerism
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
synthetic methods
title Enantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-19T04%3A46%3A43IST&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=Enantioselective%20Intramolecular%20Benzylic%20C%EF%A3%BFH%20Bond%20Amination:%20Efficient%20Synthesis%20of%20Optically%20Active%20Benzosultams&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Ichinose,%20Masami&rft.date=2011-10-10&rft.volume=50&rft.issue=42&rft.spage=9884&rft.epage=9887&rft.pages=9884-9887&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201101801&rft_dat=%3Cproquest_cross%3E1093478905%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=1093478905&rft_id=info:pmid/21913287&rfr_iscdi=true