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Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers

E. J. Alvarez-Manzaneda*, R. Chabouna, E. Alvarez, E. Cabrera, R. Alvarez-Manzaneda, A. Haidour, J. M. Ramos

*Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain, Email: eamrugr.es

E. J. Alvarez-Manzaneda, R. Chabouna, E. Alvarez, E. Cabrera, R. Alvarez-Manzaneda, A. Haidour, J. M. Ramos, Synlett, 2006, 1756-1758.

DOI: 10.1055/s-2006-947356


Abstract

The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.

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proposed mechanism



Key Words

cyclizations, diols, ethers, tetrahydrofurans, tetrahydropyrans, natural products, stereoselectivity, cerium(IV) ammonium nitrate


ID: J60-Y2006-4520