Chiral Phosphoric Acid Catalyzed Enantioselective Aza-Michael Addition of Aromatic Amines to Nitroolefins

Chiral phosphoric acid was found to be an effective organocatalyst in the enantioselective aza-Michael addition of aromatic amines to nitroolefins giving the corresponding β-nitroamine products in good yields (65%-95%) with moderate to good enantiomeric excess (16%-70%). This study represents the first example of a chiral phosphoric acid catalyzed asymmetric aza-Michael addition reaction.

摘要：以轴手性联萘酚为原料, 合成了一系列手性磷酸催化剂, 并首次将其应用于催化芳香胺和硝基烯烃的不对称氮杂迈克尔加成反应中, 产物 β-硝基胺的产率和对映选择性分别达 65%–95% 和 16%–70%.

Graphical abstractThis communication reports the enantioselective aza-Michael addition of aromatic amines to nitroolefins catalyzed by chiral phosphoric acid.Figure optionsDownload full-size imageDownload as PowerPoint slide