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Displacement of α-triflates of 2,3,4-all cis-substituted γ-lactones by sodium azide in DMF gives kinetically an azide with inversion of configuration at the C-2 of the lactone; under the reaction conditions, the initially formed azide epimerises to the apparently more crowded and thermodynamically stable all cis-azide, giving intermediates which should readily allow the incorporation of polyhydroxylated amino acids into combinatorial libraries.

Original publication




Journal article


Chemical Communications

Publication Date



1271 - 1272