844657-52-9Relevant academic research and scientific papers
Fine-tunable organocatalysts bearing multiple hydrogen-bonding donors for construction of adjacent quaternary and tertiary stereocenters via a michael reaction
Zhang, Zhi-Hai,Dong, Xiu-Qin,Chen, Dong,Wang, Chun-Jiang
supporting information; experimental part, p. 8780 - 8783 (2009/09/25)
The fine-tunable bifunctional amine/thiourea organocatalysts, relying on multipe hydrogen-bonding donors was investigated. A representative set of aryl and alkyl substituted nitroolefins were surveyed under the optimal experimental conditions. The trisubstituted carbon nucleophiles were examined with a 10 mol% of catalyst. The significant role of the multiple hydrogen-bonding donors played in the system was demonstrated through the control experiments using less bulky methylated (1R,2R,1'R,2'R)-II-E, (1R,2R,S)-II-F, and (1R,2R,R)-II-G as the catalyst under the optimized reaction condition. The fine tunable amine/thiourea organocatalysts, relying on multiple hydrogen-binding donors, showed excellent activity, diastereoselectivity, enantioselectivity, and structural scope in asymmetric Michael addition of α-substituted β-ketoesters to nitroolefins.
