The enantioselective organocatalytic Michael addition of anthrone to nitroalkenes was investigated using chiral primary amine thiourea. All the screened thioureas based on (1R,2R)-1,2-di-phenylethane-1,2-diamine could promote the reaction between anthrone and β-nitrostyrene (80%～95% yields), and the thiourea 4a afforded good enantioselectivity. Treatment of anthrone with dif-ferent β-nitrostyrenes in the presence of 5 mol% organocatalyst 4a and 5 mol% benzoic acid in ether provided the desired Michael products with excellent chemical yields (95%～98% yields) and good enantioselectivities (up to 86% ee).

Key words: Michael addition, enantioselective organocatalysis, primary amine thiourea, anthrone