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Yttrium-Catalysed Highly Stereoselective Ring-Opening Polymerization of Functional Racemic β-Lactones

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Yttrium-Catalysed Highly Stereoselective Ring-Opening Polymerization of Functional Racemic β-Lactones

As part of the ongoing exploration of the stereoselective ring-opening polymerization (ROP) of β-lactones promoted by yttrium-based catalysts developed within the OMC team (https://iscr.univ-rennes1.fr/omc/ox...), Romain Ligny et al. established the first stereoselective controlled ROP of a specific family of racemic functional β-lactones, namely 4-alkoxy-methylene-β-propiolactones (BPLORs). This process is catalysed by yttrium catalysts stabilized by nonchiral tetradentate amino-alkoxy-bisphenolate ligands (ONOOR’2)2-, combining both a good activity and a high degree of control over the molar masses of the resulting functional poly(3-hydroxyalkanoate)s PHBORs. A simple modification of ortho,para-R’ substituents on the ligand platform allows a complete reversal from virtually pure syndioselective (Ps up to 0.91 with R’ = cumyl) to pure isoselective (Pi up to 0.93 with R’ = C1) ROP, as supported by DFT insights. This is the first example of a highly isoselective ROP of a racemic chiral β-lactone.

Read more about this work in Angewandte Chemie International Edition,

http://onlinelibrary.wiley.com/doi/...

[R. Ligny PhD grant financially supported in part by the Region Bretagne]
[PhD supervisors : Dr S. Guillaume and Pr J.-F. Carpentier]