Concepedia

Stereocontrolled oxidation of 5-hydroxyalkenes with rhenium oxide. III

Suhan Tang, Robert M. Kennedy

Tetrahedron Letters · 1992 · 52 citations · 14 references

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Abstract

5-Hydroxyalkenes react with rhenium (VII) oxide (Re2O7) to provide 2-hydroxymethyl-tetrahydrofurans. Oxidation occurs with overall syn addition to the alkene. Stereoselectivity is easily understood by invoking [2+2] cycloaddition followed by reductive elimination.

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