Cinchona alkaloid derived primary amine thioureas organocatalyzed Michael addition of nitroalkanes to enones in good yield and up to 98% ee and offered a new way to construct quaternary stereocenters from enones and nitroalkanes.

The addition of nitroalkanes to α,β-unsaturated aldehydes under the catalysis of (S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine and lithium acetate as additive afforded γ-nitroaldehydes in good yield and up to 97% ee.

Primary amine catalysts derived from cinchona alkaloids have emerged as readily available, highly versatile and extremely powerful catalysts in asymmetric synthesis. In particular, they exhibit superior catalytic efficacy for successfully tackling major challenges in a variety of sterically hindered carbonyl compounds, which traditional approaches have not been able to address. This review aims to once again draw attention to this relatively underutilised process by highlighting the recent developments in the application of cinchona-based primary amine catalysts in asymmetric organocatalytic reactions.