Dimerization of Lithiated Terminal Aziridines
Identifieur interne : 000248 ( Istex/Corpus ); précédent : 000247; suivant : 000249Dimerization of Lithiated Terminal Aziridines
Auteurs : David M. Hodgson ; Steven M. MilesSource :
- Angewandte Chemie [ 0044-8249 ] ; 2006-01-30.
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Abstract
Aus zwei mach eins: Die Dimerisierung enantiomerenreiner terminaler Aziridine durch Lithiierung liefert effizient N‐geschützte 2‐En‐1,4‐diamine mit vollständiger Selektivität für das E‐Olefin (siehe Schema). Die Nützlichkeit der Methode wurde durch die Synthese von (R,S,S,R)‐2,5‐Diamino‐1,6‐diphenylhexan‐3,4‐diol demonstriert, der zentralen Einheit vieler äußerst potenter HIV‐Protease‐Inhibitoren und asymmetrischer Katalysatoren.
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DOI: 10.1002/ange.200503303
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ISTEX:554446424DF91F85176616A089E4E60186FBDAB4Le document en format XML
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Hodgson Dr.</name><affiliations><json:string>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 186‐528‐5002</json:string><json:string>E-mail: david.hodgson@chem.ox.ac.uk</json:string></affiliations></json:item><json:item><name>Steven M. 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KGaA, Weinheim</licence></availability><date type="published" when="2006-01-30"></date></publicationStmt><notesStmt><note type="content-type" subtype="brief-communication" source="shortCommunication" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-S9SX2MFS-0">brief-communication</note><note type="publication-type" subtype="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="brief-communication"><analytic><title level="a" type="main" xml:lang="en">Dimerization of Lithiated Terminal Aziridines<ref type="note" target="#nss"></ref></title><author xml:id="author-0000"><persName><forename type="first">David M.</forename><surname>Hodgson</surname><roleName type="degree">Dr.</roleName></persName><email>david.hodgson@chem.ox.ac.uk</email><affiliation>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 186‐528‐5002<address><country key="GB"></country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Steven M.</forename><surname>Miles</surname><roleName type="degree">Dr.</roleName></persName><affiliation>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 186‐528‐5002<address><country key="GB"></country></address></affiliation></author><idno type="istex">554446424DF91F85176616A089E4E60186FBDAB4</idno><idno type="ark">ark:/67375/WNG-43KJ3W8L-V</idno><idno type="DOI">10.1002/ange.200503303</idno><idno type="unit">ANGE200503303</idno><idno type="toTypesetVersion">file:ANGE.ANGE200503303.pdf</idno></analytic><monogr><title level="j" type="main">Angewandte Chemie</title><title level="j" type="alt">ANGEWANDTE CHEMIE</title><idno type="pISSN">0044-8249</idno><idno type="eISSN">1521-3757</idno><idno type="book-DOI">10.1002/(ISSN)1521-3757</idno><idno type="book-part-DOI">10.1002/ange.v118:6</idno><idno type="product">ANGE</idno><imprint><biblScope unit="vol">118</biblScope><biblScope unit="issue">6</biblScope><biblScope unit="page" from="949">949</biblScope><biblScope unit="page" to="952">952</biblScope><biblScope unit="page-count">4</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2006-01-30"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><abstract xml:lang="de" style="graphical"><p><hi rend="bold">Aus zwei mach eins</hi>: Die Dimerisierung enantiomerenreiner terminaler Aziridine durch Lithiierung liefert effizient N‐geschützte 2‐En‐1,4‐diamine mit vollständiger Selektivität für das <hi rend="italic">E</hi>‐Olefin (siehe Schema). Die Nützlichkeit der Methode wurde durch die Synthese von (<hi rend="italic">R</hi>,<hi rend="italic">S</hi>,<hi rend="italic">S</hi>,<hi rend="italic">R</hi>)‐2,5‐Diamino‐1,6‐diphenylhexan‐3,4‐diol demonstriert, der zentralen Einheit vieler äußerst potenter HIV‐Protease‐Inhibitoren und asymmetrischer Katalysatoren.<figure type="box"><media mimeType="image" url="urn:x-wiley:00448249:media:ANGE200503303:content"></media><media mimeType="image/gif" url="" rendition="webLoRes"></media><media mimeType="image/gif" url="" rendition="webOriginal"></media><media mimeType="image/gif" url="" rendition="webHiRes"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">Aziridine</term><term xml:id="kwd2">Kleinringsysteme</term><term xml:id="kwd3">Lithiierungen</term><term xml:id="kwd4">Synthesemethoden</term></keywords><keywords rend="articleCategory"><term>Zuschrift</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/554446424DF91F85176616A089E4E60186FBDAB4/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>WILEY‐VCH Verlag</publisherName><publisherLoc>Weinheim</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1521-3757</doi><issn type="print">0044-8249</issn><issn type="electronic">1521-3757</issn><idGroup><id type="product" value="ANGE"></id></idGroup><titleGroup><title type="main" xml:lang="de" sort="ANGEWANDTE CHEMIE">Angewandte Chemie</title><title type="short">Angewandte Chemie</title></titleGroup></publicationMeta><publicationMeta level="part" position="60"><doi origin="wiley" registered="yes">10.1002/ange.v118:6</doi><numberingGroup><numbering type="journalVolume" number="118">118</numbering><numbering type="journalIssue">6</numbering></numberingGroup><coverDate startDate="2006-01-30">January 30, 2006</coverDate></publicationMeta><publicationMeta level="unit" type="shortCommunication" position="18" status="forIssue"><doi origin="wiley" registered="yes">10.1002/ange.200503303</doi><idGroup><id type="unit" value="ANGE200503303"></id></idGroup><countGroup><count type="pageTotal" number="4"></count></countGroup><titleGroup><title type="articleCategory">Zuschrift</title></titleGroup><copyright ownership="publisher">Copyright © 2006 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2005-09-16"></event><event type="firstOnline" date="2005-12-27"></event><event type="publishedOnlineFinalForm" date="2006-01-23"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.6 mode:FullText source:FullText result:FullText" date="2010-05-18"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-03"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-14"></event></eventGroup><numberingGroup><numbering type="pageFirst">949</numbering><numbering type="pageLast">952</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ANGE.ANGE200503303.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="13"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="46"></count></countGroup><titleGroup><title type="main" xml:lang="en">Dimerization of Lithiated Terminal Aziridines<link href="#nss"></link></title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#aa"><personName><givenNames>David M.</givenNames><familyName>Hodgson</familyName><degrees>Dr.</degrees></personName><contactDetails><email>david.hodgson@chem.ox.ac.uk</email></contactDetails></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Steven M.</givenNames><familyName>Miles</familyName><degrees>Dr.</degrees></personName></creator></creators><affiliationGroup><affiliation xml:id="aa" countryCode="GB" type="organization"><unparsedAffiliation>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 186‐528‐5002</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Aziridine</keyword><keyword xml:id="kwd2">Kleinringsysteme</keyword><keyword xml:id="kwd3">Lithiierungen</keyword><keyword xml:id="kwd4">Synthesemethoden</keyword></keywordGroup><supportingInformation><p>Supporting information for this article is available on the WWW under <url href="http://www.wiley-vch.de/contents/jc_2001/2006/z503303_s.pdf">http://www.wiley‐vch.de/contents/jc_2001/2006/z503303_s.pdf</url> or from the author.</p></supportingInformation><abstractGroup><abstract type="graphical" xml:lang="de"><p><b>Aus zwei mach eins</b>: Die Dimerisierung enantiomerenreiner terminaler Aziridine durch Lithiierung liefert effizient N‐geschützte 2‐En‐1,4‐diamine mit vollständiger Selektivität für das <i>E</i>‐Olefin (siehe Schema). Die Nützlichkeit der Methode wurde durch die Synthese von (<i>R</i>,<i>S</i>,<i>S</i>,<i>R</i>)‐2,5‐Diamino‐1,6‐diphenylhexan‐3,4‐diol demonstriert, der zentralen Einheit vieler äußerst potenter HIV‐Protease‐Inhibitoren und asymmetrischer Katalysatoren.<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:00448249:media:ANGE200503303:content"></mediaResource><mediaResource alt="thumbnail image" rendition="webLoRes" mimeType="image/gif" href=""></mediaResource><mediaResource alt="original image" rendition="webOriginal" mimeType="image/gif" href=""></mediaResource><mediaResource alt="magnified image" rendition="webHiRes" mimeType="image/gif" href=""></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta><noteGroup><note xml:id="nss"><p>We thank the EPSRC for a Research Grant (GR/S46789/01), the EPSRC National Mass Spectrometry Service Centre for providing mass spectra, Dr. A. Cowley for X‐ray crystallographic analyses, and P. Humphreys for preliminary observations and samples of aziridines <b>4 d</b> and <b>4 g</b>.</p></note></noteGroup></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Dimerization of Lithiated Terminal Aziridines</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Dimerization of Lithiated Terminal Aziridines</title></titleInfo><name type="personal"><namePart type="given">David M.</namePart><namePart type="family">Hodgson</namePart><namePart type="termsOfAddress">Dr.</namePart><affiliation>E-mail: david.hodgson@chem.ox.ac.uk</affiliation><affiliation>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 186‐528‐5002</affiliation><affiliation>E-mail: david.hodgson@chem.ox.ac.uk</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Steven M.</namePart><namePart type="family">Miles</namePart><namePart type="termsOfAddress">Dr.</namePart><affiliation>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 186‐528‐5002</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="shortCommunication" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-S9SX2MFS-0">brief-communication</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2006-01-30</dateIssued><dateCaptured encoding="w3cdtf">2005-09-16</dateCaptured><copyrightDate encoding="w3cdtf">2006</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">13</extent><extent unit="tables">1</extent><extent unit="references">46</extent></physicalDescription><abstract>Aus zwei mach eins: Die Dimerisierung enantiomerenreiner terminaler Aziridine durch Lithiierung liefert effizient N‐geschützte 2‐En‐1,4‐diamine mit vollständiger Selektivität für das E‐Olefin (siehe Schema). Die Nützlichkeit der Methode wurde durch die Synthese von (R,S,S,R)‐2,5‐Diamino‐1,6‐diphenylhexan‐3,4‐diol demonstriert, der zentralen Einheit vieler äußerst potenter HIV‐Protease‐Inhibitoren und asymmetrischer Katalysatoren.</abstract><note type="content">*We thank the EPSRC for a Research Grant (GR/S46789/01), the EPSRC National Mass Spectrometry Service Centre for providing mass spectra, Dr. A. Cowley for X‐ray crystallographic analyses, and P. Humphreys for preliminary observations and samples of aziridines 4 d and 4 g.</note><subject lang="en"><genre>keywords</genre><topic>Aziridine</topic><topic>Kleinringsysteme</topic><topic>Lithiierungen</topic><topic>Synthesemethoden</topic></subject><relatedItem type="host"><titleInfo><title>Angewandte Chemie</title></titleInfo><titleInfo type="abbreviated"><title>Angewandte Chemie</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><note type="content"> Supporting information for this article is available on the WWW under http://www.wiley‐vch.de/contents/jc_2001/2006/z503303_s.pdf or from the author.</note><subject><genre>article-category</genre><topic>Zuschrift</topic></subject><identifier type="ISSN">0044-8249</identifier><identifier type="eISSN">1521-3757</identifier><identifier type="DOI">10.1002/(ISSN)1521-3757</identifier><identifier type="PublisherID">ANGE</identifier><part><date>2006</date><detail type="volume"><caption>vol.</caption><number>118</number></detail><detail type="issue"><caption>no.</caption><number>6</number></detail><extent unit="pages"><start>949</start><end>952</end><total>4</total></extent></part></relatedItem><identifier type="istex">554446424DF91F85176616A089E4E60186FBDAB4</identifier><identifier type="ark">ark:/67375/WNG-43KJ3W8L-V</identifier><identifier type="DOI">10.1002/ange.200503303</identifier><identifier type="ArticleID">ANGE200503303</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2006 WILEY‐VCH Verlag GmbH & Co. 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