An efficient procedure for the diastereoselective dehydration of beta-hydroxy carbonyl compounds by CeCl3 center dot 7H(2)O/Nal system

Authors
Bartoli, G Bellucci, MC Petrini, M Marcantoni, E Sambri, L Torregiani, E
Citation
G. Bartoli et al., An efficient procedure for the diastereoselective dehydration of beta-hydroxy carbonyl compounds by CeCl3 center dot 7H(2)O/Nal system, ORG LETT, 2(13), 2000, pp. 1791-1793
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
13
Year of publication
2000
Pages
1791 - 1793
Database
ISI
SICI code
1523-7060(20000629)2:13<1791:AEPFTD>2.0.ZU;2-R
Abstract
The dehydration of beta-hydroxy ketones and beta-hydroxy esters is a synthe tically useful method for the conversion of these compounds to the correspo nding alpha,beta-unsaturated derivatives. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile acts as an eff icient reagent for this conversion. The present procedure, which utilizes c heap and "friendly" reagents, offers the corresponding (E)-enones in good y ields as the only isolable products.