Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines

Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines

The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to car...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2005-01, Vol.7 (1), p.43-46
Hauptverfasser: Evans, Paul, McCabe, Thomas, Morgan, Ben S, Reau, Sophie
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 46
container_issue 1
container_start_page 43
container_title Organic letters
container_volume 7
creator Evans, Paul
McCabe, Thomas
Morgan, Ben S
Reau, Sophie
description The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.
doi_str_mv 10.1021/ol0480123
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67340521</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67340521</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-6e0e97dbba205755439b54b2a713726d84ba0be5ceba45c1f9cca90d4f49990e3</originalsourceid><addsrcrecordid>eNptkMtKHEEUhgtRvEyy8AWkNgouOta123I3jJoETAKZZN3U5TTTUt2ldQnMzm1e0ydJywyTjav_5_DxwfkROqXkEyWMXgVPxDWhjO-hYyoZrxoi2f6u1-QInaT0SAidLuoQHVFZM6EafoxebkMxHvBPcMXmPow4dHixtr63eB7DoPNUlsV3YdRD7yDdvL78xXP8PfwBj79BXgWHuxBxXgFerscpUp_eJKzCenSYV_O49tWymJT7XDK4nX7oR0gf0EGnfYKP25yh3_d3vxZfqocfn78u5g-V5o3KVQ0EVOOM0YzIRkrBlZHCMN1Q3rDaXQujiQFpwWghLe2UtVoRJzqhlCLAZ-hi432K4blAyu3QJwve6xFCSW3dcDGtRifwcgPaGFKK0LVPsR90XLeUtG9zt7u5J_ZsKy1mAPef3O47AecbQNvUPoYSx-nHd0T_ADS3hto</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67340521</pqid></control><display><type>article</type><title>Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines</title><source>American Chemical Society Journals</source><creator>Evans, Paul ; McCabe, Thomas ; Morgan, Ben S ; Reau, Sophie</creator><creatorcontrib>Evans, Paul ; McCabe, Thomas ; Morgan, Ben S ; Reau, Sophie</creatorcontrib><description>The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0480123</identifier><identifier>PMID: 15624973</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2005-01, Vol.7 (1), p.43-46</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-6e0e97dbba205755439b54b2a713726d84ba0be5ceba45c1f9cca90d4f49990e3</citedby><cites>FETCH-LOGICAL-a379t-6e0e97dbba205755439b54b2a713726d84ba0be5ceba45c1f9cca90d4f49990e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol0480123$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0480123$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15624973$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Evans, Paul</creatorcontrib><creatorcontrib>McCabe, Thomas</creatorcontrib><creatorcontrib>Morgan, Ben S</creatorcontrib><creatorcontrib>Reau, Sophie</creatorcontrib><title>Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkMtKHEEUhgtRvEyy8AWkNgouOta123I3jJoETAKZZN3U5TTTUt2ldQnMzm1e0ydJywyTjav_5_DxwfkROqXkEyWMXgVPxDWhjO-hYyoZrxoi2f6u1-QInaT0SAidLuoQHVFZM6EafoxebkMxHvBPcMXmPow4dHixtr63eB7DoPNUlsV3YdRD7yDdvL78xXP8PfwBj79BXgWHuxBxXgFerscpUp_eJKzCenSYV_O49tWymJT7XDK4nX7oR0gf0EGnfYKP25yh3_d3vxZfqocfn78u5g-V5o3KVQ0EVOOM0YzIRkrBlZHCMN1Q3rDaXQujiQFpwWghLe2UtVoRJzqhlCLAZ-hi432K4blAyu3QJwve6xFCSW3dcDGtRifwcgPaGFKK0LVPsR90XLeUtG9zt7u5J_ZsKy1mAPef3O47AecbQNvUPoYSx-nHd0T_ADS3hto</recordid><startdate>20050106</startdate><enddate>20050106</enddate><creator>Evans, Paul</creator><creator>McCabe, Thomas</creator><creator>Morgan, Ben S</creator><creator>Reau, Sophie</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050106</creationdate><title>Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines</title><author>Evans, Paul ; McCabe, Thomas ; Morgan, Ben S ; Reau, Sophie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-6e0e97dbba205755439b54b2a713726d84ba0be5ceba45c1f9cca90d4f49990e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Evans, Paul</creatorcontrib><creatorcontrib>McCabe, Thomas</creatorcontrib><creatorcontrib>Morgan, Ben S</creatorcontrib><creatorcontrib>Reau, Sophie</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Evans, Paul</au><au>McCabe, Thomas</au><au>Morgan, Ben S</au><au>Reau, Sophie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-01-06</date><risdate>2005</risdate><volume>7</volume><issue>1</issue><spage>43</spage><epage>46</epage><pages>43-46</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15624973</pmid><doi>10.1021/ol0480123</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2005-01, Vol.7 (1), p.43-46
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_67340521
source American Chemical Society Journals
title Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T18%3A01%3A40IST&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=Double%20Reduction%20of%20Cyclic%20Aromatic%20Sulfonamides:%E2%80%89%20A%20Novel%20Method%20for%20the%20Synthesis%20of%202-%20and%203-Aryl-Substituted%20Cyclic%20Amines&rft.jtitle=Organic%20letters&rft.au=Evans,%20Paul&rft.date=2005-01-06&rft.volume=7&rft.issue=1&rft.spage=43&rft.epage=46&rft.pages=43-46&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0480123&rft_dat=%3Cproquest_cross%3E67340521%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=67340521&rft_id=info:pmid/15624973&rfr_iscdi=true