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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
Author(s) -
Mangelinckx Sven,
Kostić Marina,
Backx Simon,
Petrović Biljana,
De Kimpe Norbert
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900542
Subject(s) - cyclopropane , chemistry , bicyclic molecule , ring (chemistry) , hexane , saponification , dicarboxylic acid , total synthesis , cyclopropanation , alkyl , stereochemistry , organic chemistry , ketone , medicinal chemistry , catalysis
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.