This project aims to develop a novel method for the preparation of ?-amino butanoic acid (GABA) derivatives � one which utilizes CO2 as a C-1 building block via transition metal-mediated synthesis. The synthesis of novel artificial amino acids remains a subject of considerable interest and ?-amino acids have demonstrated a broad range of biological activity such as antibacterial, antidepressant, anti-inflammatory, and anticonvulsant activity. However, current synthetic methodologies for accessing them require many reaction steps and purifications. This project proposes a more efficient route using CO2. Our proposed methodology begins with the incorporation of CO2 to form a 5-membered zirconacycle. Reaction with Eschenmoser's Salt via transmetallation to copper is followed by hydrolysis to afford the desired ?-amino acids. Our procedure offers an expansion of the synthetic methodologies available to access a wide range of ?-amino acids.

Zirconium-mediated synthesis of γ-amino acids from carbon dioxide

243rd National Meeting (2012)

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