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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 519-523

Asymmetric protonation of silyl enolates catalyzed by chiral phosphine-silver(I) complexes

Akira Yanagisawa, Taichiro Touge and Takayoshi Arai

Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage, Chiba 263-8522, Japan

Abstract: A catalytic asymmetric protonation of trimethylsilyl enolates was achieved using a 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP)-silver(I) fluoride complex as a chiral catalyst in a mixed solvent consisting of dichloromethane and methanol. Various nonracemic ketones possessing a tertiary asymmetric carbon at the α-position were prepared with high enantioselectivity up to 99 % ee.