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Synthesis 2011(1): 65-68  
DOI: 10.1055/s-0030-1258317
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Synthetic Approach for N-Acyl Imines of Trichloropyruvate

Petro P. Onys’ko*, Yaroslav Y. Khomutnyk, Tetyana V. Kim, Olena I. Kyselyova, Yuliya V. Rassukana, Volodymyr S. Brovarets, Anatoly D. Synytsya
Institute of Organic Chemistry, National Academy of Sciences, 5 Murmans’ka St, Kiev 02660, Ukraine
Fax: +380(44)5732643; e-Mail: onysko@rambler.ru;
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Publikationsverlauf

Received 2 August 2010
Publikationsdatum:
25. Oktober 2010 (online)

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Abstract

A convenient synthesis for N-acyl imines of trichloropyruvates [2-(acylimino)-3,3,3-trichloropropanoates] based on consecutive silylation-chlorinative desilylation of readily accessible α-(acylamino)-substituted dichloroacrylates was developed. The use of the 2-iminopropanoates obtained for the amidoalkylation of S-, O-, N-, and C-centered nucleophiles to afford amino acids derivatives is disclosed.

Key words

N-acyl imines - enamides - iminocarboxylates - trichloromethyl - silylation - chlorination - nucleophilic addition

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