Effect of High Pressure on the Organocatalytic Asymmetric Michael Reaction: Highly Enantioselective Synthesis of γ-Nitroketones with Quaternary Stereogenic Centers

Abstract

The significant effect of hydrostatic pressure on the difficult organocatalytic 1,4-conjugate addition of nitroalkanes to prochiral sterically congested β,β-disubstituted enones is demonstrated. This approach allows for the synthesis of γ-nitroketones containing quaternary stereogenic centers with good yields, excellent enantioselectivity, and low loading (1-5 mol %) of simple chiral primary amine catalysts.