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An Efficient Procedure for the Diastereoselective Dehydration of β-Hydroxy Carbonyl Compounds by CeCl3·7H2O/NaI System

Giuseppe Bartoli, Maria C. Bellucci, Marino Petrini, Enrico Marcantoni*, Letizia Sambri and Elisabetta Torregiani

*Dipartimento di Scienze Chimiche, Universitą di Camerino, via S. Agostino 1, I-62032 Camerino, Italy, Email:

G. Bartoli, M. C. Bellucci, M. Petrini, E. Marcantoni, L. Sambri, E. Torregiani, Org. Lett., 2000, 2, 1791-1793.

DOI: 10.1021/ol005766i

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The combination of cerium(III) chloride heptahydrate with sodium iodide mediates a useful dehydration of β-hydroxy ketones and β-hydroxy esters to the corresponding α,β-unsaturated derivatives in refluxing acetonitrile. This method, which uses cheap and friendly reagents, provides the corresponding (E)-isomers in good yields as the only isolable products.

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Key Words

enones, α,β-unsaturated esters

ID: J54-Y2000