Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc-Copper-Mediated SN2′ Alkylation

摘要

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.