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- Title
Synthesis and Catalytic Activity of Organocatalysts Based on Enaminone and Benzenediamine Hydrogen Bond Donors.
- Authors
Ciber, Luka; Požgan, Franc; Brodnik, Helena; Štefane, Bogdan; Svete, Jurij; Grošelj, Uroš
- Abstract
A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl enaminones with (S)-quininamine (9 examples) and the 1,2-benzenediamine-type catalysts were prepared in 3 steps from (S)-quininamine and ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evaluated in the Michael addition of acetylacetone to trans-β-nitrostyrene. Enantioselectivities of up to 72% ee were observed.
- Subjects
CATALYTIC activity; HYDROGEN bonding; TERTIARY amines; NITROALKENES; CATALYSTS; ACETYLACETONE; ORGANOCATALYSIS
- Publication
Catalysts (2073-4344), 2022, Vol 12, Issue 10, p1132
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal12101132