Asymmetric Synthesis of Sterically and Electronically Demanding Linear ω-Trifluoromethyl Containing Amino Acids via Alkylation of Chiral Equivalents of Nucleophilic Glycine and Alanine
journal contributionposted on 2011-01-21, 00:00 authored by Jiang Wang, Daizong Lin, Shengbin Zhou, Xiao Ding, Vadim A. Soloshonok, Hong Liu
An operationally convenient, scalable asymmetric synthesis of linear, ω-trifluoromethyl-containing amino acids, which were not previously produced in their enantiomerically pure form, has been developed via alkylation of chiral equivalents of nucleophilic glycine and alanine. The simplicity of the experimental procedures and high stereochemical outcome (yields up to 90% and diastereoselectivity up to 99%) of the presented method render these fluorinated amino acids readily available for systematic medicinal chemistry studies and de novo peptide design.
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ContainingalaninesimplicityStericallychiral equivalentsstereochemical outcomeacidAlkylationprocedureLinearnucleophilic glycineenantiomericallyTrifluoromethylmethodsynthesisChiral EquivalentsAsymmetric Synthesisscalablediastereoselectivitypeptide designAlanineAnNucleophilic GlycineyieldalkylationAcidchemistry studiesElectronicallyAmino