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Bismuth Triflate-Chiral Bipyridine Complexes as Water-Compatible Chiral Lewis Acids

Shu Kobayashi,* Tsuyoshi Ogino, Haruka Shimizu, Shunpei Ishikawa, Tomoaki Hamada and Kei Manabe

*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: skobayasmol.f.u-tokyo.ac.jp

S. Kobayashi, T. Ogino, H. Shimizu, S. Ishikawa, T. Hamada, K. Manabe, Org. Lett., 2005, 7, 4729-4731.

DOI: 10.1021/ol051965w (free Supporting Information)


Abstract

Highly enantioselective hydroxymethylation of silicon enolates with an aqueous formaldehyde solution has been developed using a chiral bismuth complex as a Lewis acid. Bi(OTf)3 is unstable in the presence of water but is stabilized by the basic ligand.

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Scandium(III) Fluoride as a Novel Catalyst for Hydroxymethylation of Dimethylsilyl Enolates in Aqueous Media

M. Kokubo, S. Kobayashi, Synlett, 2008, 1562-1564.


Key Words

Mukaiyama aldol addition, silyl enol ethers


ID: J54-Y2005-1720