J. Am. Chem. Soc., 126 (39), 12236 -12237, 2004. 10.1021/ja047896i S0002-7863(04)07896-5
Web Release Date: September 11, 2004

Copyright © 2004 American Chemical Society

Catalytic Asymmetric Hydroxymethylation of Silicon Enolates Using an Aqueous Solution of Formaldehyde with a Chiral Scandium Complex

Shunpei Ishikawa, Tomoaki Hamada, Kei Manabe, and Sh Kobayashi*

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

skobayas@mol.f.u-tokyo.ac.jp

Received April 12, 2004

Abstract:

Catalytic asymmetric hydroxymethylation of silicon enolates has been achieved. In this reaction, an aqueous solution of formaldehyde can be used to realize an easy and safe procedure, and high enantioselectivities have been obtained. This is the first example of catalytic asymmetric reactions in aqueous media with a chiral scandium complex.

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