Radical reactivity of α,β,β-trifluoroacrylic ester: Facile approach to γ-silyloxy-α,β,β-trifluorobutyric acid derivatives involving regioselective nucleophilic radical addition reaction

Abstract

In this paper are disclosed new aspects for chemical reactivity of benzyl α,β,β-trifluoroacrylate, which is already known to undergo CC bond formation reactions via nucleophilic addition-elimination reaction or Diels-Alder cycloaddition reaction. The α,β,β-trifluoroacrylate reacted well with nucleophilic radical species, generated from cyclic ethers, to afford the corresponding radical adducts in good to excellent yield as a diastereomeric mixture. The radical addition protocol is successfully evolved into the new synthetic approach to γ-silyloxy-α,β,β-trifluorobutanoic acid derivatives, which fascinates as promising precursors for medicinally as well as pharmaceutically-important organic molecules.