Efficient synthesis of chiral α,β-epoxyesters via a cyclic sulfate intermediate

Article abstract of DOI:10.1016/S0040-4039(98)00190-7

An efficient synthesis of chiral α,β-epoxyester 1 from chiral 2,3- dihydroxyester 2 has been developed. Ester 2 is converted to the corresponding cyclic surfate 3, which is opened with either LiBr in THF or Bu₄NBr in acetone at rt to furnish 2-bromo-3-hydroxyester 4. Treatment of 4 with K₂CO₃ in methanol at low temperature gives α,β-epoxyester 1 in excellent overall yield and in the same ee as in the starting diol.