Asymmetric domino Michael-Henry reaction of 1,2-diones with nitroolefins catalyzed by a chiral bisoxazolidine-Ni(acac)2 complex

Article abstract of DOI:10.1016/j.tetasy.2014.06.011

The asymmetric domino Michael-Henry reaction of 1,2-cyclohexadione with nitroolefins catalyzed by chiral ligand bisoxazolidine 1 and Ni(acac) ₂ has been developed. This process provided highly functionalized chiral bicycle[3,2,1] octane derivatives with the generation of four new stereogenic centers in high yields (76-99%), and with excellent enantioselectivities (up to 99%) and good diastereoselectivities (up to 9:1) under mild reaction conditions. The procedure presented is simple and makes this method suitable for practical use.