Synthesis of new optically active α,α′,β-trisubstituted-β-lactones as monomers for stereoregular biopolyesters.

ABSTRACT Various optically active (4 R)-alkyloxycarbonyl-3,3-dialkyl-2-oxetanones as monomers were synthesized from L-( S)-malic acid in six steps to prepare a new family of stereopolyesters for biomedical applications. The synthesis began with an esterification followed of a dialkylation in the aim to introduce hydrophobic groups as methyl or reactive group as allyl. Then, a saponification has permitted to obtain the corresponding diacids that reacted with appropriate alcohols to furnish different monoesters. The last and most important step was activation of hydroxyl group of monoesters with the asymmetric carbon configuration inversion according to the Mitsunobu reaction. Thus, this reaction has provided lactones from monoesters with 100% enantiomeric excess which was confirmed by 1H NMR and by the synthesis of corresponding isotactic and semicrystalline homopolyesters. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2586-2597 [ABSTRACT FROM AUTHOR]