Synthesis of substituted cyclopropanes from 1,3-diols through the corresponding cyclic sulfates

Article abstract of DOI:10.1016/0040-4020(95)00708-G

The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol %) leads to the corresponding substituted cyclopropanes 3 through a γ-elimination process, the sulfate ion acting as leaving group.