Catalytic asymmetric conjugate addition of α-fluoro β-ketophosphonates to nitroalkenes in the presence of nickel complexes

•This is the first example of catalytic conjugate addition of α-fluoro β-ketophosphonates to nitroalkenes using chiral transition metal.•Excellent diastereoselectivities (10–50:1), enantioselectivities (93–99% ee), and high yields were observed.•This reaction conditions is mild and stable in air- and moisture.•This synthetic method is highly efficient catalytic system (1 mol% of catalyst).

The catalytic enantioselective conjugate addition reaction of α-fluoro β-ketophosphonates to nitroalkenes promoted by chiral nickel complexes is described. Treatment of α-fluoro β-ketophosphonates with nitroalkenes under mild reaction conditions afforded the corresponding Michael adducts containing fluorinated quaternary stereogenic center with excellent enantioselectivity (up to >99% ee).

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide