Synthesis and Catalytic Activity of Organocatalysts Based on Enaminone and Benzenediamine Hydrogen Bond Donors

A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and enaminone or 1,2-benzenediamine hydrogen bond donors were synthesized. The enaminone-type catalysts prepared by the transamination N,N-dimethyl enaminones with (9 examples) 1,2-benzenediamine-type in 3 steps from ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evaluated Michael addition acetylacetone to trans-β-nitrostyrene. Enantioselectivities up 72% ee observed.