MARTIN, Anthony; ROBERT, Frédéric; TATON, Daniel; CRAMAIL, Henri; VINCENT, Jean-Marc; LANDAIS, Yannick

doi:10.1002/chem.201402373

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MARTIN, Anthony
Institut des Sciences Moléculaires [ISM]

ROBERT, Frédéric
Institut des Sciences Moléculaires [ISM]

TATON, Daniel

Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering

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Chemistry - A European Journal. 2014, vol. 20, n° 37, p. 11946-11953

Wiley-VCH Verlag

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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.< Leer menos

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CHROMATOGRAPHIC-SEPARATION

(RS)-ALPHA-METHYLBENZYL METHACRYLATE

OPTICALLY-ACTIVE POLYMERS

FUNCTIONAL THEORY CALCULATIONS

ENANTIOSELECTIVE CYCLOPOLYMERIZATION

MUKAIYAMA ALDOL REACTION

ALPHA-OLEFINS

anhydrides

desymmetrization

enantioselectivity

organocatalysis

polyesters

polymerization

ASYMMETRIC-SELECTIVE POLYMERIZATION

VIBRATIONAL CIRCULAR-DICHROISM

RING-OPENING POLYMERIZATION

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

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