Bismuth triflate-chiral bipyridine complexes as water-compatible chiral Lewis acids

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.