Synthesis of racemic 2-(aminomethyl)cyclopropane-1,1-dicarboxylic acid as a new constrained γ-amino dicarboxylic acid bypassing alkyl 3-aza-2-oxobicyclo[3.1.0]hexane-1-carboxylates

The first synthesis of racemic 2-(aminomethyl)cyclopropane-1,1-dicarboxylic acid was developed involving sequential iodocarbocyclization, azidation, saponification and reduction of dimethyl 2-allylmalonate. The developed synthetic pathway avoids reactions such as ring opening of the cyclopropane ring toward acyclic delta-amino carboxylic acid derivatives or lactamisation toward bicyclic methyl 3-aza-2-oxobicyclo[3.1.0]hexane-1-carboxylates which occur in alternative synthetic strategies.