Session: General Topics: New Synthesis & Characterization of Polymers:

Multi-component reactions (MCRs) have been gathering intensive attentions from polymer community due to their synthetic modularity and click-type reactivity. In this study, we selected the Pteasis three-component reaction (Petasis-3CR), which is a powerful tool to generate the α-amino acids by reacting the aromatic boronic acids, amines, and glyoxylic acids. Despite the synthetic benefits arising from the Petasis-3CR, chemical nature of boronic acids remains problematic for polymer synthesis. To be precise, boronic acids are known to be in equilibrium with their corresponding cyclic trimers of boroxines, suppressing their employment in polymer structures due to the lack of chemical stoichiometry and a potential risk to behave as a cross-linker. Therefore, we have decided to tackle the improvement of the Petasis-3CR aiming the integration with polymer chemistry. In this presentation, the original Petasis-3CR was engineered so that the protocol would be compatible with polymer synthesis, offering an access to poly (α-amino acids) in one-pot manner (Scheme).

Scheme. A modified Petasis three-component reaction for polymer synthesis.

Scheme. A modified Petasis three-component reaction for polymer synthesis.

Mr. Li Chieh Chou

Gunma University

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