Asymmetric anti-Selective Michael Reaction of Imidazole-Modified Ketones with trans-β-Nitroalkenes

The successful application of imidazole-modified ketones in asymmetric anti-selective Michael reactions with trans-beta-nitroalkenes is presented by employing a newly developed 3-bromothiophene-modified chiral diamine ligand. The corresponding conjugate adduct was submitted to further transformations with Grignard reagents to solve the problem of a-site selectivity of simple linear ketones. Additionally, the syn-selective product was obtained by treating the anti-selective adduct with a simple base. In this way, the site-specific products for both diastereomers in the asymmetric conjugate addition of simple ketones to nitroalkenes can be obtained.