Diazo functionalities have gained interest among researchers for their broad use as building blocks in synthesis. Shaikh et al. have previously reported on the functionalization and transformation of diazo keto esters now seeks to explore further uses for such compounds. The increased reactivity of the carbon at the diazo site makes these compounds prime candidates for transformations that are traditionally restricted to other functional groups, which usually requires extra steps of protection and deprotection thus incurring a higher cost with more synthetic steps. Amino acids, specifically cyclopropyl amino acids, have also gained recent attention in their applicability towards pharmaceuticals. The demand for new ways of synthesizing these cyclopropyl compounds has been a noticeable focus in research lately and thus we provide a method to transform a synthesized diazo keto ester into a cyclopropyl β-amino acid with nitro styrene and a copper catalyst, followed by a simple hydrogenation and hydrolysis.

Synthesis of amino acids via diazo keto ester transformation

255th National Meeting (2018)

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