Asymmetric Mannich-type Reactions of Fluorinated Ketoesters with Binaphthyl-Modified Thiourea Catalysts

Abstract

The catalytic enantioselective Mannich-type reaction promoted by chiral binaphthyl-modified bifunctional organocatalysts is described. The treatment of <TEX>${\alpha}$</TEX>-fluoro-<TEX>${\beta}$</TEX>-ketoesters with N-Boc imines under mild reaction conditions afforded the corresponding <TEX>${\beta}$</TEX>-aminated <TEX>${\alpha}$</TEX>-fluoro-<TEX>${\beta}$</TEX>-ketoesters with excellent enantioselectivities (up to 98% ee).