To evaluate the synthetic potential of this catalytic system, a gram-scale reaction of α,β-unsaturated 2-acyl imidazole 2a (657 mg/3.10 mmol) with 5-aminopyrazole 1a (800 mg/3.72 mmol) was conducted in the presence of 2.2 mol % of L1 and 2.0 mol % of Ni(OTf)2 in DCM at room temperature. Gratifyingly, the reaction proceeded smoothly to afford 3a in 95% yield with 98% ee (eq 1, Scheme 4). To sum up, we have developed a newly prepared C2symmetric chiral bipyridine-N,N'-dioxides from optically pure (1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride and successfully applied them to synthesize chiral pyrazolo [3,4-b]pyridine analogues. In the presence of 5.5 mol % of L1 and 5.0 mol % of Ni(OTf)2 in DCM at room temperature, the corresponding products were obtained in good to excellent yields (85-97%) with excellent enantioselectivities (up to 99%). 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.