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Highly Syndiotactic or Isotactic Polyhydroxyalkanoates by Ligand-Controlled Yttrium-Catalyzed Stereoselective Ring-Opening Polymerization of Functional Racemic β-Lactones

Abstract : Reported herein is the first stereoselective controlled ROP of a specific family of racemic functional β-lactones, namely 4-alkoxymethylene-β-propiolactones (BPL(OR) s). This process is catalyzed by an yttrium complex stabilized by a nonchiral tetradentate amino alkoxy bisphenolate ligand _ONOO(R'2) ₍2-) , which features both a good activity and a high degree of control over the molar masses of the resulting functional poly(3-hydroxyalkanoate)s. A simple modification of the R' substituents in ortho and para position on the ligand platform allows for a complete reversal from virtually pure syndioselectivity (Ps up to 0.91 with R'=cumyl) to very high isoselectivity (Pi up to 0.93 with R'=Cl), as supported by DFT insights. This is the first example of a highly isoselective ROP of a racemic chiral β-lactone.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01579647
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Submitted on : Thursday, August 31, 2017 - 2:41:14 PM
Last modification on : Friday, July 10, 2020 - 4:21:56 PM

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Romain Ligny, Mikko M. Hänninen, Sophie M. Guillaume, Jean-François Carpentier. Highly Syndiotactic or Isotactic Polyhydroxyalkanoates by Ligand-Controlled Yttrium-Catalyzed Stereoselective Ring-Opening Polymerization of Functional Racemic β-Lactones. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2017, 56 (35), pp.10388-10393. ⟨10.1002/anie.201704283⟩. ⟨hal-01579647⟩

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