Asymmetric aza-Michael additions of 4-nitrophthalimide to nitroalkenes and preliminary study of the products for herbicidal activities

The first application of 4-nitrophthalimide as nitrogen nucleophile for enantioselective aza-Michael addition to nitroalkenes has been developed. The process is promoted by chiral thiourea catalyst derived from cinchonine to give corresponding Michael adducts with up to 87% ee. Activity test showed that some products of the reaction have moderate or good herbicidal activity against cole and barnyard grass at 100 μg/ml.