Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 37, Pages 11946-11953Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402373
Keywords
anhydrides; desymmetrization; enantioselectivity; organocatalysis; polyesters; polymerization
Categories
Funding
- CNRS
- MNERT
- Region Aquitaine
- ANR (Chirpol) [09-BLAN-0178-02]
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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.
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