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

Shū 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
Org. Lett., 2005, 7 (21), pp 4729–4731
DOI: 10.1021/ol051965w
Publication Date (Web): September 13, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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

Abstract

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Catalytic asymmetric hydroxymethylation of silicon enolates with an aqueous formaldehyde solution has been developed using a chiral bismuth complex. This is the first example of highly enantioselective reactions using a chiral bismuth catalyst in aqueous media. In this paper, we have added Bi(OTf)3−1 complex as a “water-compatible Lewis acid”. Bi(OTf)3 is unstable in the presence of water but is stabilized by the basic ligand.

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History

  • Published In Issue October 13, 2005
  • Received August 14, 2005

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