Reductive Amination/Cyclization of Methyl Levulinate with Aspartic Acid: Towards Renewable Polyesters with a Pendant Lactam Unit

ChemSusChem. 2019 Jul 19;12(14):3370-3376. doi: 10.1002/cssc.201900745. Epub 2019 Jun 11.


Environmental regulation and depletion of fossil resources are boosting the search for new polymeric materials produced from biomass. Here, the synthesis of a new diester bearing a pendant lactam unit from methyl levulinate and aspartic acid is reported. The palladium-catalyzed reductive amination/cyclization sequence was carefully optimized to afford the diacid with high yield (>95 %). In a second step, the compound was esterified to give the corresponding diester. The latter monomer was copolymerized with α-ω linear diols, yielding polyesters with molecular weights up to 20.5 kg mol-1 .

Keywords: aspartic acid; biobased polyesters; levulinic acid; polymers; reductive amination.

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