Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry

Aaron Aponick* and Berenger Biannic

*Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States, Email: aponickchem.ufl.edu

A. Aponick, B. Biannic, Org. Lett., 2011, 13, 1330-1333.

DOI: 10.1021/ol200203k

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Abstract

The gold(I)-catalyzed cyclization of chiral monoallylic diols to form tetrahydropyrans is highly stereoselective. Substrates that differ only in olefin geometry provide enantiomeric products from formal S_N2′ reactions in high yields with excellent chirality transfer. The allylic alcohol stereochemistry also efficiently controls the facial selectivity when the substrates include additional stereocenters.

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Key Words

Tetrahydropyrans

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ID: J54-Y2011-0690