A Practical Approach Towards the Asymmetric Synthesis of α,γ-Substituted γ-Sultones

Abstract

The first auxiliary controlled synthesis of enantiopure α,γ-substituted γ-sultones via α-allylated chiral sulfonates is described. The high asymmetric inductions of the α-allylations were reached with our previously described auxiliary 1,2:5,6-di-O-isopropylidene-α-d-allofuranose (de≥98%). Cleavage of the auxiliary and successive diastereoselective ring closure of the sulfonic acid intermediates led to the title compounds in high selectivities (de, ee≥98%) and good to excellent yields (52-90%). Enantiopure α,γ-substituted γ-sultones are interesting intermediates in the reaction with various nucleophiles.