Concise Asymmetric Synthesis of β‐Trifluoromethylated α,β‐Diamino Esters through Addition Reactions of Glycine Esters to CF3‐Sulfinylimine

Abstract

Abstract(S)‐N‐(tert‐Butylsulfinyl)‐3,3,3‐trifluoroacetaldimine underwent reactions with enolates of glycine esters with quite remarkable stereochemical results, that is, with virtually complete (>99 % de) diastereoselectivity and excellent (>98 %) yields. Furthermore, the reactions are conducted under operationally convenient conditions (Cs2CO3‐catalyzed, ambient temperature) to provide the most advanced, general, and scalable access to biologically important β‐trifluoromethylated α,β‐diamino acids.