Organocatalyzed Step-Growth Polymerization through Desymmetrization of Cyclic Anhydrides: Synthesis of Chiral Polyesters
| dc.rights.license | open | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | MARTIN, Anthony | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | ROBERT, Frédéric | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 1 LCPO : Polymerization Catalyses & Engineering | |
| dc.contributor.author | TATON, Daniel | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 2 LCPO : Biopolymers & Bio-sourced Polymers | |
| dc.contributor.author | CRAMAIL, Henri | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | VINCENT, Jean-Marc | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | LANDAIS, Yannick | |
| dc.date.accessioned | 2020 | |
| dc.date.available | 2020 | |
| dc.date.issued | 2014 | |
| dc.identifier.issn | 0947-6539 | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/20246 | |
| dc.description.abstractEn | The 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.iso | en | |
| dc.publisher | Wiley-VCH Verlag | |
| dc.subject.en | CHROMATOGRAPHIC-SEPARATION | |
| dc.subject.en | (RS)-ALPHA-METHYLBENZYL METHACRYLATE | |
| dc.subject.en | OPTICALLY-ACTIVE POLYMERS | |
| dc.subject.en | FUNCTIONAL THEORY CALCULATIONS | |
| dc.subject.en | ENANTIOSELECTIVE CYCLOPOLYMERIZATION | |
| dc.subject.en | MUKAIYAMA ALDOL REACTION | |
| dc.subject.en | ALPHA-OLEFINS | |
| dc.subject.en | anhydrides | |
| dc.subject.en | desymmetrization | |
| dc.subject.en | enantioselectivity | |
| dc.subject.en | organocatalysis | |
| dc.subject.en | polyesters | |
| dc.subject.en | polymerization | |
| dc.subject.en | ASYMMETRIC-SELECTIVE POLYMERIZATION | |
| dc.subject.en | VIBRATIONAL CIRCULAR-DICHROISM | |
| dc.subject.en | RING-OPENING POLYMERIZATION | |
| dc.title.en | Organocatalyzed Step-Growth Polymerization through Desymmetrization of Cyclic Anhydrides: Synthesis of Chiral Polyesters | |
| dc.type | Article de revue | |
| dc.identifier.doi | 10.1002/chem.201402373 | |
| dc.subject.hal | Chimie/Polymères | |
| bordeaux.journal | Chemistry - A European Journal | |
| bordeaux.page | 11946-11953 | |
| bordeaux.volume | 20 | |
| bordeaux.hal.laboratories | Laboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629 | * |
| bordeaux.issue | 37 | |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.institution | Université de Bordeaux | |
| bordeaux.peerReviewed | oui | |
| hal.identifier | hal-01366215 | |
| hal.version | 1 | |
| hal.origin.link | https://hal.archives-ouvertes.fr//hal-01366215v1 | |
| bordeaux.COinS | ctx_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 |
Files in this item
| Files | Size | Format | View |
|---|---|---|---|
|
There are no files associated with this item. |
|||