Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols
Identifieur interne : 001B81 ( Istex/Corpus ); précédent : 001B80; suivant : 001B82Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols
Auteurs : Youwei Xie ; Paul E. FloreancigSource :
- Angewandte Chemie International Edition [ 1433-7851 ] ; 2013-01-07.
English descriptors
- KwdEn :
- Absolute stereochemistry, Allylic, Allylic alcohol, Allylic alcohol transposition, Allylic alcohols, Angew, Angewandte communications, Bidirectional stereogenesis, Cascade, Cascade reactions, Catalyst, Chem, Epoxide, Epoxide group, Epoxide opening, Equilibration, Hydroxy group, Ketone, Molecular complexity, Reaction conditions, Rhenium, Rhenium oxide, Room temperature, Single stereoisomer, Stereochemical, Stereochemical conduits, Stereochemical equilibration, Stereochemical information, Stereogenic centers, Thermodynamic control, Transposing alcohol, Transposing alcohols, Transposition, Verlag gmbh, Weinheim angew.
- Teeft :
- Absolute stereochemistry, Allylic, Allylic alcohol, Allylic alcohol transposition, Allylic alcohols, Angew, Angewandte communications, Bidirectional stereogenesis, Cascade, Cascade reactions, Catalyst, Chem, Epoxide, Epoxide group, Epoxide opening, Equilibration, Hydroxy group, Ketone, Molecular complexity, Reaction conditions, Rhenium, Rhenium oxide, Room temperature, Single stereoisomer, Stereochemical, Stereochemical conduits, Stereochemical equilibration, Stereochemical information, Stereogenic centers, Thermodynamic control, Transposing alcohol, Transposing alcohols, Transposition, Verlag gmbh, Weinheim angew.
Abstract
Complexity from simplicity: Polycyclic ethers are synthesized by cascade reactions involving the use of epoxides as electrophilic traps in the transposition of allylic alcohols. Stereogenic centers are created by functionalizing prochiral sites under thermodynamic control, and remote stereoinduction can be achieved through the use of ketones as conduits.
Url:
DOI: 10.1002/anie.201208132
Links to Exploration step
ISTEX:776BFACA960B0DC3328CABE3128C7297310E6038Le document en format XML
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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2012-10-09"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:3.2.0 mode:FullText" date="2013-02-26"></event><event type="publishedOnlineEarlyUnpaginated" date="2012-11-22"></event><event type="publishedOnlineFinalForm" date="2012-12-28"></event><event type="firstOnline" date="2012-11-22"></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:4.6.4 mode:FullText" date="2015-10-02"></event></eventGroup><numberingGroup><numbering type="pageFirst">625</numbering><numbering type="pageLast">628</numbering></numberingGroup><correspondenceTo>Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ANIE.ANIE201208132.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="8"></count><count type="tableTotal" number="0"></count><count type="referenceTotal" number="67"></count></countGroup><titleGroup><title type="main" xml:lang="en">Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols<link href="#nss"></link></title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Youwei</givenNames><familyName>Xie</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#aa" corresponding="yes"><personName><honorifics>Prof.</honorifics><givenNames>Paul E.</givenNames><familyName>Floreancig</familyName></personName><contactDetails><email>florean@pitt.edu</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="aa" countryCode="US" type="organization"><unparsedAffiliation>Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">cascade reactions</keyword><keyword xml:id="kwd2">isomerization</keyword><keyword xml:id="kwd3">oxygen heterocycles</keyword><keyword xml:id="kwd4">rearrangement</keyword><keyword xml:id="kwd5">stereoselectivity</keyword></keywordGroup><fundingInfo><fundingAgency>National Institutes of Health</fundingAgency><fundingNumber>P50‐GM06082</fundingNumber></fundingInfo><fundingInfo><fundingAgency>National Science Foundation</fundingAgency><fundingNumber>CHE‐1151979</fundingNumber></fundingInfo><supportingInformation><p>As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
</p><supportingInfoItem><mediaResource alt="supporting information" href="urn-x:wiley:14337851:media:anie201208132:anie_201208132_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="graphical" xml:lang="en"><p><b>Complexity from simplicity</b>: Polycyclic ethers are synthesized by cascade reactions involving the use of epoxides as electrophilic traps in the transposition of allylic alcohols. Stereogenic centers are created by functionalizing prochiral sites under thermodynamic control, and remote stereoinduction can be achieved through the use of ketones as conduits.<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:14337851:media:ANIE201208132:content"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta><noteGroup><note xml:id="nss"><p>This work was supported by grants from the National Institutes of Health (P50‐GM06082) and the National Science Foundation (CHE‐1151979). We thank Dr. Steve Geib for crystallographic analyses, and Dr. Damodaran Krishnan and Sage Bowser for assistance with NMR experiments.</p></note></noteGroup></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols</title></titleInfo><name type="personal"><namePart type="given">Youwei</namePart><namePart type="family">Xie</namePart><affiliation>Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="termsOfAddress">Prof.</namePart><namePart type="given">Paul E.</namePart><namePart type="family">Floreancig</namePart><affiliation>Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</affiliation><affiliation>E-mail: florean@pitt.edu</affiliation><affiliation>Correspondence address: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</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">2013-01-07</dateIssued><dateCaptured encoding="w3cdtf">2012-10-09</dateCaptured><copyrightDate encoding="w3cdtf">2013</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">8</extent><extent unit="tables">0</extent><extent unit="references">67</extent></physicalDescription><abstract>Complexity from simplicity: Polycyclic ethers are synthesized by cascade reactions involving the use of epoxides as electrophilic traps in the transposition of allylic alcohols. Stereogenic centers are created by functionalizing prochiral sites under thermodynamic control, and remote stereoinduction can be achieved through the use of ketones as conduits.</abstract><note type="content">*This work was supported by grants from the National Institutes of Health (P50‐GM06082) and the National Science Foundation (CHE‐1151979). We thank Dr. Steve Geib for crystallographic analyses, and Dr. Damodaran Krishnan and Sage Bowser for assistance with NMR experiments.</note><note type="funding">National Institutes of Health - No. P50‐GM06082; </note><note type="funding">National Science Foundation - No. CHE‐1151979; </note><subject lang="en"><genre>keywords</genre><topic>cascade reactions</topic><topic>isomerization</topic><topic>oxygen heterocycles</topic><topic>rearrangement</topic><topic>stereoselectivity</topic></subject><relatedItem type="host"><titleInfo><title>Angewandte Chemie International Edition</title></titleInfo><titleInfo type="abbreviated"><title>Angew. Chem. 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