Exploiting the Addition of Trimethyl(trifluoromethyl)silane to Functionalized N-Benzylimines for the Preparation of Two Novel x-Trifluoromethyl x-Amino Acids
13 February 2012 (eFirst)
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.
amino acids - alkylations - fluorine - peptidomimetics - imines