1160175-63-2Relevant academic research and scientific papers
Amino acid-based synthesis of trifluoromethylalkene dipeptide isosteres by alcohol-assisted nucleophilic trifluoromethylation and organozinc-copper- mediated SN2′ alkylation
Kobayashi, Kazuya,Narumi, Tetsuo,Oishi, Shinya,Ohno, Hiroaki,Fujii, Nobutaka
scheme or table, p. 4626 - 4629 (2009/09/08)
(Chemical Equation Presented) A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of γ-keto esters and SN2′ alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the SN2′ reaction is also discussed.
