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

Straightforward gram-scale syntheses of a novel gamma-trifluoromethyl gamma-amino acid and a novel epsilon-trifluoromethyl-epsilon-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 us...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 44; no. 6; pp. 903 - 908
Main Authors Tkachenko, Anton N., Radchenko, Dmytro S., Mykhailiuk, Pavel K., Shishkin, Oleg V., Tolmachev, Andrei A., Komarov, Igor V.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOPHILIC TRIFLUOROMETHYLATION
ALDIMINES
ENANTIOMERS
amino acids
imines
CONFORMATION
PERFLUOROALKYLATION
INHIBITION
ENZYME
alkylations
AMINOTRANSFERASE
CATALYZED TRIFLUOROMETHYLATION
peptidomimetics
fluorine
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Summary:Straightforward gram-scale syntheses of a novel gamma-trifluoromethyl gamma-amino acid and a novel epsilon-trifluoromethyl-epsilon-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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1289702