485818-75-5Relevant academic research and scientific papers
Synthesis of novel bifunctional Michael acceptors
Urbaneja, Laura Mediavilla,Krause, Norbert
, p. 4467 - 4470 (2007/10/03)
The conjugated dienones 1a, 1c-e, and 1g were synthesized by aldol reaction of cyclohex-2-enones 3 with aldehydes or ketones and subsequent elimination. Whereas the acetone adducts could be converted into the desired products 1a/g by treatment with CeCl3·7H2O/Nal, the dienones 1c-e were obtained by Appel bromination and dehydrobromination with triethylamine. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3·7H2O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone
Bartoli, Giuseppe,Bosco, Marcella,Dalpozzo, Renato,Giuliani, Arianna,Marcantoni, Enrico,Mecozzi, Tiziana,Sambri, Letizia,Torregiani, Elisabetta
, p. 9111 - 9114 (2007/10/03)
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 β-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.
