Diastereoselective Synthesis of Polysubstituted Tetrahydropyrans and Thiacyclohexanes via Indium Trichloride Mediated Cyclizations

Xiao-Fan Yang, Joel T. Mague and Chao-Jun Li*

*Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, Email: cj.limcgill.ca

X.-F. Yang, J. T. Mague, C.-J. Li, J. Org. Chem., 2001, 66, 739-747.

DOI: 10.1021/jo001136i

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Abstract

InCl₃ mediates cyclizations between homoallyl (thio)alcohols with aldehydes to provide polysubstituted tetrahydropyrans and thiacyclohexanes in high yields with excellent diastereoselectivities. The configuration of the tetrahydropyrans depends on the geometry of the homoallyl alcohols; whereas both cis- and trans-homoallyl mercaptans provide the same major diastereomers.

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proposed mechanism

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Key Words

Tetrahydropyrans, Prins Reaction

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ID: J42-Y2001