Chirality-Directed Regioselectivity: An Approach for the Synthesis of Alternating Poly(Lactic-co-Glycolic Acid)
journal contributionposted on 2021-03-09, 15:39 authored by Yiye Lu, Jordan H. Swisher, Tara Y. Meyer, Geoffrey W. Coates
We report the synthesis of alternating poly(lactic-co-glycolic acid) via a regioselective ring-opening polymerization of (S)-methyl glycolide. An enantiopure aluminum salen catalyst with binaphthyl backbone facilitates the regioselective ring-opening of this unsymmetrical cyclic diester exclusively at the glycolide acyl–oxygen bond site. This living, chain-growth polymerization is able to reach low dispersities with tailored molecular weights. Quantitative regioselectivity calculations and sequence error analysis have been established for this sequence-controlled polymer.
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regioselective ring-opening polymer...siteacylregioselective ring-openingApproachglycolic acidenantiopure aluminum salen catalystchain-growth polymerizationsequence-controlled polymersynthesismethylunsymmetrical cyclic diestersequence error analysisdispersitieGlycolicChirality-Directed RegioselectivityPolyglycolideQuantitative regioselectivity calcu...Synthesibinaphthyl backbonebond