An Efficient Procedure for the Diastereoselective Dehydration of beta-Hydroxy Carbonyl Compounds by CeCl(3).7H(2)O/NaI System.
The dehydration of beta-hydroxy ketones and beta-hydroxy esters is a synthetically useful method for the conversion of these compounds to the corresponding alpha,beta-unsaturated derivatives. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile acts as an efficient reagent for this conversion. The present procedure, which utilizes cheap and "friendly" reagents, offers the corresponding (E)-enones in good yields as the only isolable products.
Bartoli
G
Dipartimento di Scienze Chimiche, Università di Camerino, via S. Agostino 1, I-62032 Camerino, Italy, and Dipartimento di Chimica Organica "A. Mangini", Università di Bologna, viale Risorgimento 4, I-40136 Bologna, Italy.
Bellucci
MC
Petrini
M
Marcantoni
E
Sambri
L
Torregiani
E