Exploiting the Addition of Trimethyl(trifluoromethyl)silane
to Functionalized N-Benzylimines for
the Preparation of Two Novel x-Trifluoromethyl x-Amino Acids

Anton N. Tkachenko; Dmytro S. Radchenko; Pavel K. Mykhailiuk; Oleg V. Shishkin; Andrei A. Tolmachev; Igor V. Komarov

doi:10.1055/s-0031-1289702

PAPER

Exploiting the Addition of Trimethyl(trifluoromethyl)silane to Functionalized N-Benzylimines for the Preparation of Two Novel x-Trifluoromethyl x-Amino Acids

Anton N. Tkachenko^a,b, Dmytro S. Radchenko^a,b, Pavel K. Mykhailiuk*^a,b, Oleg V. Shishkin^c,d, Andrei A. Tolmachev^a,b, Igor V. Komarov^a,b
^a Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine
^b Department of Chemistry, Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, 01033 Kyiv, Ukraine
^c SSI, Institute for Single Crystals, National Academy of Science of Ukraine, 60 Lenina Ave., 61001 Kharkiv, Ukraine
^d Department of Inorganic Chemistry V. N., Karazin Kharkiv National University, Vul. Svobody 4, 61022 Kharkiv, Ukraine
e-Mail: Pavel.Mykhailiuk@gmail.com;

Abstract

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Abstract

Straightforward gram-scale syntheses of a novel γ-trifluoromethyl γ-amino acid and a novel ε-trifluoromethyl-ε-amino acid are described. The key step in both syntheses is an acid-catalyzed nucleophilic trifluoromethylation of a cyclic N-benzylimine possessing an ester group by using the Ruppert--Prakash reagent [trimethyl(trifluoromethyl)silane]. The strategy provides a potentially general approach for the synthesis of x-trifluoromethyl x-amino acids.

Key words

amino acids - alkylations - fluorine - peptidomimetics - imines

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