Synthesis 2008(20): 3356-3359  
DOI: 10.1055/s-0028-1083160
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Dehydrative Cyclization of Allylic Diols

Aaron Aponick*, Berenger Biannic
Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
Fax: +1(352)8460296; e-Mail: [email protected];
Further Information

Publication History

Received 18 July 2008
Publication Date:
25 September 2008 (online)

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.

    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.