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: eamr
ugr.es
E. J. Alvarez-Manzaneda, R. Chabouna, E. Alvarez, E. Cabrera, R. Alvarez-Manzaneda, A. Haidour, J. M. Ramos, Synlett, 2006, 1756-1758.
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.
see article for more examples
proposed mechanism
Key Words
cyclizations, diols, ethers, tetrahydrofurans, tetrahydropyrans, natural products, stereoselectivity, cerium(IV) ammonium nitrate
ID: J60-Y2006-4520
