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Synthesis 2011(21): 3426-3428  
DOI: 10.1055/s-0030-1260249
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© Georg Thieme Verlag Stuttgart ˙ New York

Methyl α-Iminotrifluoropropionate: A Novel Convenient Building Block for the Preparation of Functionalized Derivatives Bearing a Trifluoroalanine Residue

Yuliya V. Rassukana*
Institute of Organic Chemistry, National Academy of Sciences, 5 Murmans’ka St, Kiev 02660, Ukraine
Fax: +380(44)5732643; e-Mail: juravi@rambler.ru;
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Publication History

Received 21 July 2011
Publication Date:
05 October 2011 (online)

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Abstract

A convenient synthesis of methyl α-iminotrifluoropropionate (methyl 3,3,3-trifluoro-2-iminopropanoate, 3), based on the aza-Wittig reaction of methyl trifluoropyruvate with triphenylphosphine imide, was developed. The synthetic potential of N-H imine 3, existing as equilibrium mixture (10:1) of E/Z isomers, in the preparation of functionalized acyclic and heterocyclic derivatives possessing a pharmacophoric trifluoroalanine fragment, is disclosed.

Key words

N-H imines - trifluoropyruvate - trifluoroalanine - iminocarboxylates - cyclization - nucleophilic addition

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