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Synlett 2014; 25(07): 987-990
DOI: 10.1055/s-0033-1340953
DOI: 10.1055/s-0033-1340953
letter
Asymmetric Organocatalytic Cyclopropanation on Chiral Menthyl Acrylate for the Synthesis of (–)-trans-2-Aminomethylcyclopropanecarboxylic Acid [(–)-TAMP]
Weitere Informationen
Publikationsverlauf
Received: 29. Januar 2014
Accepted after revision: 17. Februar 2014
Publikationsdatum:
14. März 2014 (online)


Abstract
An enantioselective synthesis of (–)-trans-2-aminomethylcyclopropanecarboxylic acid [(–)-TAMP], a partial agonist for GABAc receptor, has been achieved as the hydrochloride salt in 3.9% overall yield for total eight steps from l-menthol. The synthesis features double asymmetric cyclopropanation that employs cinchona alkaloid derived organocatalyst and l-menthyl chiral auxiliary.