Chirality-Directed Regioselectivity: An Approach for the Synthesis of Alternating Poly(Lactic-<i>co</i>-Glycolic Acid)
Yiye Lu, Jordan H. Swisher, Tara Y. Meyer, Geoffrey W. Coates
Abstract
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.
Topics & Concepts
RegioselectivityEnantiopure drugGlycolic acidChemistryChirality (physics)PolymerizationRing-opening polymerizationRing (chemistry)Lactic acidPolymer chemistrySequence (biology)StereochemistryCatalysisPolymerOrganic chemistryEnantioselective synthesisBiochemistryBiologyBacteriaPhysicsChiral symmetry breakingQuantum mechanicsQuarkGeneticsNambu–Jona-Lasinio modelbiodegradable polymer synthesis and propertiesCarbon dioxide utilization in catalysisAdvanced Polymer Synthesis and Characterization