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Lewis acid-catalyzed asymmetric hydroxymethylation of silicon enolates in aqueous media
Authors:Kei Manabe  Shunpei Ishikawa  Tomoaki Hamada  Sh Kobayashi
Institution:

Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract:Asymmetric hydroxymethylation of silicon enolates with formaldehyde in aqueous media has been achieved using praseodymium triflate and a chiral crown ether. Formaldehyde aqueous solution can be directly used for the reactions, and a water/THF mixture was found to be the best solvent system. This is the first example of catalytic asymmetric hydroxymethylation of silicon enolates.
Keywords:Lewis acid  aldol reaction  hydroxymethylation
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