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  • Conformationally Rigid Trifluoromethyl-Substituted α-Amino Acid Designed for Peptide Structure Analysis by Solid-State 19F NMR Spectroscopy

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

Synthesis , 2012, 44 (06), 903-908

DOI: 10.1055/s-0031-1289702

Tkachenko A. N.; Radchenko D. S.; Mykhailiuk P. K.; Shishkin O. V.; Tolmachev A. A.; Komarov I. V.

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.

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

Tkachenko A. N.; Radchenko D. S.; Mykhailiuk P. K.; Shishkin O. V.; Tolmachev A. A.; Komarov I. V.
Synthesis 2012, 44 (06), 903-908
DOI: 10.1055/s-0031-1289702

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