Asymmetric conjugate addition of nitroalkanes to enones with a chiral α-aminophosphonate catalyst

Chiral diethyl (2R)-tetrahydropyrro-2-ylphosphonate is an effective catalyst for the Michael addition of nitroalkanes to α,β-unsaturated ketones. This study revealed that the hydrate salt of this α-aminophosphonate was found to be a better catalytic species. Moderate to high enantioselectivities were achieved in reactions that tolerate various nitroalkanes and enones in the presence of low loading of both catalyst (10 mol %) and bulk base (25 mol %).

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide