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pubmed-article:12467442pubmed:abstractText2-Alkylidenecycloalkanones are powerful synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective beta-elimination reaction to (E)-2-alkylidenecycloalkanones in 2-(1-hydroxyalkyl)cycloalkanones. The synthetic value of the present procedure is demonstrated by the synthesis of monoterpene (S)-(-)-pulegone (8) in its optically active form.lld:pubmed
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pubmed-article:12467442pubmed:dateRevised2006-11-15lld:pubmed
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pubmed-article:12467442pubmed:articleTitleAn efficient procedure for the preparation of (E)-alpha-alkylidenecycloalkanones mediated by a CeCl(3) x 7H(2)O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone.lld:pubmed
pubmed-article:12467442pubmed:affiliationDepartment of Chemical Sciences, University of Camerino, via S. Agostino 1, I-62032 Camerino (MC), Italy.lld:pubmed
pubmed-article:12467442pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:12467442pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed