1215067-69-8Relevant academic research and scientific papers
Dual organocatalytic ion-pair assemblies: A highly efficient approach for the enantioselective oxa-michael-mannich reaction of salicylic aldehydes with cyclohexenones
Xia, Ai-Bao,Xu, Dan-Qian,Luo, Shu-Ping,Jiang, Jun-Rong,Tang, Jie,Wang, Yi-Feng,Xu, Zhen-Yuan
supporting information; experimental part, p. 801 - 804 (2010/06/11)
A study was conducted to demonstrate a novel type of bifunctional catalyst generated by the self-assembly of pyrrolidines and readily available primary amino acids. It was demonstrated that the protonation of the aromatic nitrogen atom of pyrrolidines by amino acids spontaneously led to ion-pair assemblies. The self-assembled catalysts possessed dual activation centers and enabled the catalysis of the electrophilic and nucleophilic substrates similar to catalysis by enzymes. The simultaneous activation of cyclohex-2-enone and salicylic aldehyde by pyrrolidines and amino acids generated the transient ion pairs through iminiums and imines. The resultant assemblies ensured that the enantioselective domino oxa-Michael addition and intramolecular Mannich reaction proceeded to afford the corresponding products upon hydrolysis.
