A highly efficient asymmetric synthesis of α,γ-substituted γ-amino sulfonates via
diastereoselective ring-opening of enantiopure α,γ-substituted γ-sultones with inversion
of configuration at the attacked γ-carbon is described. In the key step sodium azide
is used as the nucleophilic nitrogen source. Secondary and tertiary γ-amino sulfonates
were synthesized in very good yields and excellent diastereo- and enantiomeric excesses
(de, ee ≥98%).
amino sulfonates - sultones - asymmetric synthesis - ring-opening - azide
