4-Alkyloxycarbonyl-2-oxetanones and 3-alkyl-4-alkyloxycarbonyl-2-oxetanones as versatile chiral precursors in the design of functionalized polyesters with a controlled architecture

Abstract

The necessity for accessing a very large variety of high-molecular-weight racemic and optically active polyesters aimed at biomedical or chemical applications has led to the growth of a large series of racemic and optically active 4-alkyloxycarbonyl-2-oxetanones and 3-alkyl-4-alkyloxycarbonyl-2-oxetanones. Different synthesis routes have been established to prepare these monomers according to the bound ester group structure and the required enantiomeric or diastereomeric excess. The basic molecules were aspartic acid, malic acid or their 3-alkyl derivatives. The introduced ester group can be chiral, reactive, hydrophobic, hydrophilic or bioactive. The major interest in this enlarged monomer family lies in the possibility of have at one's disposal β-substituted β-lactones with very strict control of the stereogenic center configuration. This property is important with regard to the tailoring of well-defined polymeric materials. A second benefit lies in the tailor-making of complex architectures by the copolymerization of two or more β-substituted β-lactones. In al cases, the resulting materials have the composition of the monomer feed and a completely controlled configurational structure.

Keywords:

• 4-Alkyloxycarbonyl-2-oxetanones
• 3-alkyl-4-alkyloxycarbonyl-2-oxetanones
• beta-substituted beta-lactones
• poly(beta-malic acid) derivatives
• functionalized polyesters
• biomedical field