An 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

Giuseppe Bartoli; Marcella Bosco; Renato Dalpozzo; Arianna Giuliani; Enrico Marcantoni; Tiziana Mecozzi; Letizia Sambri; Elisabetta Torregiani

doi:10.1021/jo026418s

An 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

J Org Chem. 2002 Dec 13;67(25):9111-4. doi: 10.1021/jo026418s.

Authors

Giuseppe Bartoli¹, Marcella Bosco, Renato Dalpozzo, Arianna Giuliani, Enrico Marcantoni, Tiziana Mecozzi, Letizia Sambri, Elisabetta Torregiani

Affiliation

¹ Department of Chemical Sciences, University of Camerino, via S. Agostino 1, I-62032 Camerino (MC), Italy.

PMID: 12467442
DOI: 10.1021/jo026418s

Abstract

2-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes / chemical synthesis*
Catalysis
Chemistry, Organic / methods*
Cyclohexane Monoterpenes
Magnetic Resonance Spectroscopy
Molecular Structure
Monoterpenes / chemical synthesis*
Monoterpenes / chemistry
Stereoisomerism

Substances

Alkanes
Cyclohexane Monoterpenes
Monoterpenes
pulegone