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

Abstract

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 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 δ-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.