Multigram Synthesis of Diastereomerically Pure Tetrahydrofuran-diols

Abstract

A highly efficient protocol for the large-scale oxidative cyclization of 1,5-dienes is described. This convenient ruthenium(VIII)-catalyzed (0.2 mol%) cyclization reaction allows the preparation of cis-2,5-disubstituted tetrahydrofurans in high yields (up to 92%) and excellent diastereomeric ratio (>95:5 dr). This simple and reliable method is insensitive to moisture and air and can, therefore, be carried out in an open reaction vessel.

ruthenium - oxidation - cyclization - heterocycle - diastereoselectivity

References

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