Synthetic routes for Y-BiPy ligand：Taking into account the convenience and diversity, we have designed two synthetic pathways for preparation of these bipyridines. One method involves the late-stage alkylation to introduce the substituted pyridine moieties, while the other utilizes the late-stage palladium-catalyzed cross-coupling reaction to introduce various substituents at the 3,3'-positions of binaphthyl skeleton. The first synthetic procedure commenced with chiral naphthalene-2-carboxylic acid 1, which yielded the 3,3'functionalized derivative 2 through a palladium-catalyzed carboxylic acid-directed orthoarylation reaction. Subsequently, the carboxylic acid is transformed into the corresponding diester, followed by reduction and bromination to give the dibromide 3. The last double alkylation of 5H-cyclopenta[2,1-b:3,4-b']dipyridine derivatives with 3 worked smoothly in the presence of excesses of NaH, resulting the formation of final chiral bipyridines L1-L2 in moderate yields. These nitrogen-containing bidentate chiral ligands are also known as 4,5-diazafluorenes, which traditionally have been considered as less effective ligands than un-linked bipyridines due to the large bite angle, resulting a decreased overlap between the nitrogen lone pairs and the metal orbitals. However, despite this perception, 4,5-diazafluorene ligands have demonstrated excellent performances in a series of catalytic reactions. Therefore, we embarked on an investigation into their performance in transition-metal-catalyzed asymmetric reactions. Diaryliodoniums act as powerful reagents for arylation of nucleophiles in both asymmetric and non-asymmetric reactions. In our prior work, we successfully accomplished copper-catalyzed enantioselective nucleophilic ring-opening reaction of cyclic diaryliodoniums with primary amines. However, the secondary amines were unfortunately beyond the substrate scope, resulting in poor yields and low enantioselectivity possibly due to the increased steric hindrance. These results are likely due to the strong coordination ability of secondary amines with the copper catalyst. Additionally, a chiral cobalt anion strategy only provides very low yields and moderate enantioselectivity for N-methyl aniline. Herein, we hypothesized that our newly prepared atropochiral planar bipyridines, with a spacious open structure, might offer a solution to this challenge. It is particularly noteworthy that the products III formed using cyclic secondary amines cannot be prepared through simple alkylation reactions from axially chiral amine I.