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Paper | Regular issue | Vol 27, No. 2, 1988, pp.457-473
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4393
Syntheses of α,β-Unsaturated Ketones Starting from Vinylic and Allylic Grignard Reagents via 2-Imidazolylmethanol Intermediates

Satoshi Hayakawa, Tohru Michiue, Masao Okamoto,* Shoko Hatakeyama, and Shunsaku Ohta

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


Various α , β -unsaturated ketones (9,12 and 16) were prepared from 2-alkanol-1-methyl-1H-imidazoles (6,10 and 13 respectively), which were obtained by treatment of 2-acyl-lmethyl-lH-imidazoles (1) with vinylic Grignard reagents, a lithium acetylide and allylic Grignard reagents, respectively. dl-(ar)-Turmerone (16i) was also synthesized as an application of the present methodology.