Scandium(III) Fluoride as a Novel Catalyst for Hydroxymethylation of Dimethylsilyl Enolates in Aqueous Media
Masaya Kokubo, Shu Kobayashi*
*Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: shu_kobayashichem.s.u-tokyo.ac.jp
M. Kokubo, S. Kobayashi, Synlett, 2008, 1562-1564.
Hydroxymethylation of dimethylsilyl (DMS) enolates using aqueous formaldehyde solution is catalyzed by scandium(III) fluoride in aqueous media to give the corresponding β-hydroxy ketones in good to excellent yields, but TMS enolates react sluggishly under the same conditions. ScF3 has been shown to be a unique catalyst for this reaction.
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S. Kobayashi, T. Ogino, H. Shimizu, S. Ishikawa, T. Hamada, K. Manabe, Org. Lett., 2005, 7, 4729-4731.