Water enables diastereodivergency in bispidine-based chiral amine-catalyzed asymmetric Mannich reaction of cyclic <i>N</i>-sulfonyl ketimines with ketones
Gonglin Li, Yan Zhang, Hongkun Zeng, Xiaoming Feng, Zhishan Su, Lili Lin
Abstract
-HIV-1 activity are obtained in excellent yields and good to excellent ee values. Control experiments and density functional theory (DFT) calculations were applied to study the diastereodivergent mechanism, which reveal that the diastereodivergent catalysis should be state-determined, and the water reverses the energies of states to realize the diastereodivergency. The findings are quite new and might inspire more diastereodivergent asymmetric synthesis.
Topics & Concepts
CatalysisChemistrySulfonylAmine gas treatingEnantioselective synthesisCombinatorial chemistryMannich reactionDensity functional theoryComputational chemistryOrganic chemistryAlkylSynthesis and Catalytic ReactionsAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis