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Synthesis of racemic 2-(aminomethyl)cyclopropane-1,1-dicarboxylic acid as a new constrained U+03B3-amino dicarboxylic acid bypassing alkyl 3-aza-2-oxobicyclo[3.1.0]hexane-1-carboxylates

Journal Contribution - Journal Article

Subtitle:Synthesis of racemic 2-(aminomethyl)cyclopropane-1,1-dicarboxylic acid as a new constrained gamma-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.
Journal: European Journal of Organic Chemistry
ISSN: 1434-193X
Issue: 31-32
Volume: 2019
Pages: 5187 - 5189
Publication year:2019