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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

Authors
  • Mangelinckx, Sven
  • Kostić, Marina
  • Backx, Simon
  • Petrović, Biljana
  • De Kimpe, Norbert
Publication Date
Jan 01, 2019
Source
Ghent University Institutional Archive
Keywords
Language
English
License
Unknown
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Abstract

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.

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