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_kobayashi
chem.s.u-tokyo.ac.jp
M. Kokubo, S. Kobayashi, Synlett, 2008, 1562-1564.
DOI: 10.1055/s-2008-1078409
Abstract
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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Key Words
scandium, scandium fluoride, catalysis, β-hydroxy ketones, hydroxymethylation, aqueous media, Mukaiyama aldol addition
ID: J60-Y2008-1690
