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Organocatalyzed Step-Growth Polymerization through Desymmetrization of Cyclic Anhydrides: Synthesis of Chiral Polyesters

dc.rights.licenseopen
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorMARTIN, Anthony
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorROBERT, Frédéric
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorTATON, Daniel
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorCRAMAIL, Henri
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorVINCENT, Jean-Marc
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorLANDAIS, Yannick
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2014
dc.identifier.issn0947-6539
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20246
dc.description.abstractEnThe polymerization of prochiral bis-anhydrides with diols catalyzed by a cinchona alkaloid was shown to provide chiral polyesters in good yields and with high levels of stereocontrol. The structures of the polyesters were determined by H-1 and C-13 NMR analyses, whereas their size was estimated by both size-exclusion chromatography (SEC) and MALDI-TOF mass spectrometry, which indicated that moderate degrees of polymerization were attained through this step-growth polymerization. The enantioselectivity of the process was evaluated by using chiral HPLC analysis of the bis-lactones resulting from a controlled chemoselective degradation of the polyesters. The best stereocontrol was reached for oligomers formed from bis-anhydride and diol monomers bearing rigid aromatic spacers between the reactive functional groups. In this case, average enantioselectivities were comparable to those observed during ring-opening of simple anhydrides with similar alcohols. In contrast, the use of more flexible spacers between reactive entities generally led to lower levels of stereocontrol.
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.subject.enCHROMATOGRAPHIC-SEPARATION
dc.subject.en(RS)-ALPHA-METHYLBENZYL METHACRYLATE
dc.subject.enOPTICALLY-ACTIVE POLYMERS
dc.subject.enFUNCTIONAL THEORY CALCULATIONS
dc.subject.enENANTIOSELECTIVE CYCLOPOLYMERIZATION
dc.subject.enMUKAIYAMA ALDOL REACTION
dc.subject.enALPHA-OLEFINS
dc.subject.enanhydrides
dc.subject.endesymmetrization
dc.subject.enenantioselectivity
dc.subject.enorganocatalysis
dc.subject.enpolyesters
dc.subject.enpolymerization
dc.subject.enASYMMETRIC-SELECTIVE POLYMERIZATION
dc.subject.enVIBRATIONAL CIRCULAR-DICHROISM
dc.subject.enRING-OPENING POLYMERIZATION
dc.title.enOrganocatalyzed Step-Growth Polymerization through Desymmetrization of Cyclic Anhydrides: Synthesis of Chiral Polyesters
dc.typeArticle de revue
dc.identifier.doi10.1002/chem.201402373
dc.subject.halChimie/Polymères
bordeaux.journalChemistry - A European Journal
bordeaux.page11946-11953
bordeaux.volume20
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue37
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01366215
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01366215v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20-%20A%20European%20Journal&rft.date=2014&rft.volume=20&rft.issue=37&rft.spage=11946-11953&rft.epage=11946-11953&rft.eissn=0947-6539&rft.issn=0947-6539&rft.au=MARTIN,%20Anthony&ROBERT,%20Fr%C3%A9d%C3%A9ric&TATON,%20Daniel&CRAMAIL,%20Henri&VINCENT,%20Jean-Marc&rft.genre=article


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