Bismuth triflate-chiral bipyridine complexes as water-compatible chiral Lewis acids.
[reaction: see text] 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.
Kobayashi
Shü
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. skobayas@mol.f.u-tokyo.ac.jp
Ogino
Tsuyoshi
T
Shimizu
Haruka
H
Ishikawa
Shunpei
S
Hamada
Tomoaki
T
Manabe
Kei
K
D015082:2,2'-Dipyridyl / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D017655:Silicon Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D008698:Mesylates; D017655:Silicon Compounds; D014867:Water; C445789:Bi(OTf)3; D015082:2,2'-Dipyridyl