Michael addition reaction of malonates with nitro-olefins catalyzed by 1,1-diaminoazine, a bifunctional hydrogen bonding organocatalyst

Carbon-carbon bond forming processes are central to synthetic organic chemistry, and the Michael addition reaction is a frequently used method for C-C bond formation; many organocatalysts have been utilised to facilitate this reaction. In this article, 1,1-diaminoazine-catalysed Michael addition reaction of malonates (nucleophiles) with nitro-olefins (electrophiles) is reported. The bifunctional character of the organocatalyst facilitates the C-C bond formation. The catalytic site comprises a guanidine portion and an imine group, which helps in hydrogen bond exchange. This catalytic process affords Michael adducts with good to moderate yields over a wide range of substrates. The control experiments support the bifunctional nature of the catalyst.