Synlett 2014; 25(07): 987-990
DOI: 10.1055/s-0033-1340953
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© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Cyclopropanation on Chiral Menthyl Acrylate for the Synthesis of (–)-trans-2-Aminomethylcyclopropanecarboxylic Acid [(–)-TAMP]

Yuka Sugeno
Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan   Fax: +81(45)7872403   eMail: moikawa@yokohama-cu.ac.jp
,
Yuichi Ishikawa
Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan   Fax: +81(45)7872403   eMail: moikawa@yokohama-cu.ac.jp
,
Masato Oikawa*
Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan   Fax: +81(45)7872403   eMail: moikawa@yokohama-cu.ac.jp
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Publikationsverlauf

Received: 29. Januar 2014

Accepted after revision: 17. Februar 2014

Publikationsdatum:
14. März 2014 (online)


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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.