Gold-Catalyzed Dehydrative Cyclization of Allylic Diols

Abstract

The gold(I)-catalyzed cyclization of monoallylic diols is an efficient method for the formation of tetrahydropyrans from readily available, easily prepared substrates. The reaction has been shown to be general and high yielding with low catalyst loadings. Several new synthetically useful substrates and efficient methods for both their preparation and cyclization are reported.

Key words

allylic diol - dehydrative cyclization - tetrahydropyran - gold-catalysis - cross-metathesis

References

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7

We find that the most simple and effective workup method for this system involves direct adsorption of the reaction mixture onto silica gel followed immediately by column chromatography.