2-Amino-1,3-propane diols: A versatile platform for the synthesis of aliphatic cyclic carbonate monomers

Starting from commercially available 2-amino-1,3-propane diols, a variety of functional cyclic carbonate monomers were synthesized through a general two-step strategy. First the amino group was chemo-selectively reacted with a diverse set of electrophiles to result in functional diol intermediates (1), which were then cyclized in an intramolecular fashion to generate a series of functional aliphatic six-membered cyclic carbonate monomers (2). The unique feature of this approach is its ability to install concurrently two different functional groups. This includes a specific tethered functional group and a second functional group, which are installed in the monomer-forming reactions. Selected monomers were subjected to organo-catalytic ring opening polymerization to produce well-defined homopolymers and copolymers (EM ≥ 1.5) with controlled composition. Primary amine containing polymers were also readily accessed via post-polymerization acidolysis of a tBoc-derived monomer (2k). This approach will provide direct access to functional biodegradable polymers and impact the development of next-generation materials for biomedical and environmentally friendly products. © 2013 The Royal Society of Chemistry.