Diastereoselective access to chiral non‐racemic [1,3]oxazolo‐[2,3‐a]isoindol‐5‐one ring systems viaO‐cationic cyclization
Identifieur interne : 000A06 ( Istex/Corpus ); précédent : 000A05; suivant : 000A07Diastereoselective access to chiral non‐racemic [1,3]oxazolo‐[2,3‐a]isoindol‐5‐one ring systems viaO‐cationic cyclization
Auteurs : Jana Sikoraiová ; Štefan Marchalín ; Abderrahim Chihab-Eddine ; Adam DaïchSource :
- Journal of Heterocyclic Chemistry [ 0022-152X ] ; 2002-03.
Abstract
Dedicated to Professor Jean Morel for his retirement
Url:
DOI: 10.1002/jhet.5570390223
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ISTEX:AF6BD97E7DCF80AFAAF7F152A1BBDDD048717B5CLe document en format XML
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date="2014-10-30"></event></eventGroup><numberingGroup><numbering type="pageFirst">383</numbering><numbering type="pageLast">390</numbering></numberingGroup><correspondenceTo>Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</correspondenceTo><linkGroup><link type="toTypesetVersion" href="file:JHET.JHET5570390223.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="0"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="15"></count></countGroup><titleGroup><title type="main" xml:lang="en">Diastereoselective access to chiral non‐racemic [1,3]oxazolo‐[2,3‐<i>a</i>]isoindol‐5‐one ring systems <i>via</i><i>O</i>‐cationic cyclization<link href="#fn1"></link></title><title type="short" xml:lang="en">Diastereoselective Access to Chiral Non‐Racemic [1,3]Oxazolo‐[2,3‐<fi>a</fi>]isoindol‐5‐one</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Jana</givenNames><familyName>Sikoraiová</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>ŠTefan</givenNames><familyName>Marchalín</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Abderrahim</givenNames><familyName>Chihab‐Eddine</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af3" corresponding="yes"><personName><givenNames>Adam</givenNames><familyName>Daïch</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="SK" type="organization"><unparsedAffiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK‐812 37 Bratislava, Slovakia</unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="MA" type="organization"><unparsedAffiliation>Laboratoire de Bio‐Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="FR" type="organization"><unparsedAffiliation>Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</unparsedAffiliation></affiliation></affiliationGroup><fundingInfo><fundingAgency>Scientific Council of University of Le Havre and the Slovak Grant Agency</fundingAgency><fundingNumber>1/92/2002</fundingNumber></fundingInfo><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p><b>Dedicated to Professor Jean Morel for his retirement</b></p><p>The title compounds <b>4</b> have been prepared from suitable β‐amino‐ alcohol <b>2</b> and phthalic anhydride (<b>5</b>) in a three‐step sequence in moderate to good yields (58‐94%). The key step of this methodology is based on an intramolecular <i>O</i>‐cationic cyclization involving <i>N</i>‐acyliminium species. The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.</p></abstract></abstractGroup></contentMeta><noteGroup><note xml:id="fn1"><p>This work was presented at JCO “Journées de Chimie Organique”, Poster A‐89, École Polytechnique‐Palaiseau, France, September 11‐13 (2001).</p></note></noteGroup></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Diastereoselective access to chiral non‐racemic [1,3]oxazolo‐[2,3‐a]isoindol‐5‐one ring systems viaO‐cationic cyclization</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Diastereoselective Access to Chiral Non‐Racemic [1,3]Oxazolo‐[2,3‐a]isoindol‐5‐one</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Diastereoselective access to chiral non‐racemic [1,3]oxazolo‐[2,3‐a]isoindol‐5‐one ring systems viaO‐cationic cyclization</title></titleInfo><name type="personal"><namePart type="given">Jana</namePart><namePart type="family">Sikoraiová</namePart><affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK‐812 37 Bratislava, Slovakia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">ŠTefan</namePart><namePart type="family">Marchalín</namePart><affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK‐812 37 Bratislava, Slovakia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Abderrahim</namePart><namePart type="family">Chihab‐Eddine</namePart><affiliation>Laboratoire de Bio‐Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Adam</namePart><namePart type="family">Daïch</namePart><affiliation>Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</affiliation><description>Correspondence: Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article"></genre><originInfo><publisher>Wiley‐Blackwell</publisher><place><placeTerm type="text">Hoboken</placeTerm></place><dateIssued encoding="w3cdtf">2002-03</dateIssued><dateCaptured encoding="w3cdtf">2001-10-23</dateCaptured><copyrightDate encoding="w3cdtf">2002</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="tables">1</extent><extent unit="references">15</extent></physicalDescription><abstract>Dedicated to Professor Jean Morel for his retirement</abstract><abstract>The title compounds 4 have been prepared from suitable β‐amino‐ alcohol 2 and phthalic anhydride (5) in a three‐step sequence in moderate to good yields (58‐94%). 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The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.</abstract><note type="content">*This work was presented at JCO “Journées de Chimie Organique”, Poster A‐89, École Polytechnique‐Palaiseau, France, September 11‐13 (2001).</note><note type="funding">Scientific Council of University of Le Havre and the Slovak Grant Agency - No. 1/92/2002; </note><relatedItem type="host"><titleInfo><title>Journal of Heterocyclic Chemistry</title></titleInfo><genre type="journal">journal</genre><subject><genre>article-category</genre><topic>Article</topic></subject><identifier type="ISSN">0022-152X</identifier><identifier type="eISSN">1943-5193</identifier><identifier type="DOI">10.1002/(ISSN)1943-5193</identifier><identifier type="PublisherID">JHET</identifier><part><date>2002</date><detail type="volume"><caption>vol.</caption><number>39</number></detail><detail type="issue"><caption>no.</caption><number>2</number></detail><extent unit="pages"><start>383</start><end>390</end><total>8</total></extent></part></relatedItem><identifier type="istex">AF6BD97E7DCF80AFAAF7F152A1BBDDD048717B5C</identifier><identifier type="DOI">10.1002/jhet.5570390223</identifier><identifier type="ArticleID">JHET5570390223</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2002 Journal of Heterocyclic Chemistry</accessCondition><recordInfo><recordContentSource>WILEY</recordContentSource><recordOrigin>Wiley‐Blackwell</recordOrigin></recordInfo></mods></metadata><enrichments><json:item><type>multicat</type><uri>https://api.istex.fr/document/AF6BD97E7DCF80AFAAF7F152A1BBDDD048717B5C/enrichments/multicat</uri></json:item></enrichments><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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