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Abstract
A novel type of highly efficient chiral C2-symmetric bipyridine-N,N’-dioxides catalysts to catalyze Michael addition/Cyclization of 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts in 85-97% yield with up to 99% enantioselectivity. Remarkably, this protocol exhibits extraordinary advantages in terms of reactivity and enantioselectivity, given the fact that as low as 2.2 mol % of L1 and 2.0 mol % of Ni(OTf)2 can promote the title reaction on gram scale to afford desired product with excellent enantioselectivity.
Supplementary materials
Title
Chiral Bipyridine-N,N’-dioxides Catalysts: Design, Synthesis, and Application in Synthesis of 1H-pyrazolo[3,4-b]pyridine Analogues
Description
A novel type of highly efficient chiral C2-symmetric bipyridine-N,N’-dioxides catalysts to catalyze Michael addition/Cyclization of 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts in 85-97% yield with up to 99% enantioselectivity. Remarkably, this protocol exhibits extraordinary advantages in terms of reactivity and enantioselectivity, given the fact that as low as 2.2 mol % of L1 and 2.0 mol % of Ni(OTf)2 can promote the title reaction on gram scale to afford desired product with excellent enantioselectivity.
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