As shown in Figure , the two chiral auxiliaries were able to stereoselectively control the chirality of the staircase target in the P-configuration. Notably, unlike the two isomers in Figure , where the [C(=O)NH] scaffolds lie in the same plane as the phenyl ring as expected, in this case, the scaffold is distorted by about 30° away from the phenyl ring. This distortion is caused by repulsion between the two terminal auxiliary groups. The chiral carbon center connected to the scaffold does not follow the typical Felkin-Ahn model arrangement; instead, the planar scaffold is aligned along the C-H bond of the C(sp³) center. The steric effects of the two auxiliaries push the two phenyl plates to slip relative to each other, resulting in staircase chirality. The distance between the two phenyl rings, measured from their centers, is 3.952 Å, which is shorter than the distances observed in the two isomers shown in Figure . With this success on hand, we then turned our attention to the staircase target containing chiral tertiary amino acid and (R)-or (S)-1-phenylethan-1-amine auxiliaries; the latter auxiliary has been proven to be efficient on controlling orientational chirality. The synthesis of the first building block (15) was started from commercially available 4-bromobenzoic acid which was subjected to the treatment with oxalyl dichloride to give 4-bromobenzoyl chloride (12) (Scheme 3). This step was followed by nucleophilic reaction of ( ) with (R)-1-phenylethan-1-amine to give (R)-4-bromo-N-(1-phenylethyl)benzamide . (R)-N-(1phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide ( ) was obtained by treating with B2Pin2 in the presence of PdCl2(dppf) as the catalyst and KOAc as an additive in 1,4-dioxane. The synthesis of the first building block ( ), (R)-4-(8-bromonaphthalen-1-yl)-N-(1-phenylethyl)benzamide, was performed by conducting Suzuki-Miyaura cross coupling. The synthesis of the second building block was started from dehydration of isopropyl 2-oxo-2-phenylacetate with (R)-2-methylpropane-2-sulfinamide by using Ti(OEt)4 in dry THF at 75 o C to room temperature. 1,4-Dibromobenzene was converted into (4bromophenyl)lithium precursor via the treatment with n-BuLi in THF, which was followed by the treatment with isopropyl (S,E)-2-((tert-butylsulfinyl)imino)-2-phenylacetate ( In P-target 19, the scaffold of [C(=O)NH] is placed in the same plane of phenyl ring as anticipated. However, in M-target 20, this scaffold is distorted about 30 o away from the phenyl ring due to the repulsion by two terminal auxiliary groups, which is like the situation observed in target 11 as shown in Figure . In P-target 19, Felkin-Anh model fits both [C(=O)NH] scaffold-and N-sulfinyl amino carbon centers; but In M-target 20, Felkin-Anh model only fits N-sulfinyl amino carbon center while [C(=O)NH] scaffold is arranged nearly long C-H bond of the chiral carbon. Obviously, the remote steric effects of these two auxiliaries are responsible for the present stereochemical arrangements. The distances between two centers of phenyl rings were measured to be 3.747 Å for P-target 19, and 3.473 Å for M-target 20, respectively. Interestingly, the orientational chirality of three functional groups on tertiary carbon of P-isomer 19 and M-isomer 20 are different, i.e., Nsulfinyl amino group is pushed away from (R)-amide auxiliary in the former, but phenyl group is away from (S)-amide auxiliary in the latter. Very interestingly, M-isomer 20 displays an obvious C(sp3)-centered turbo chirality by three propellers in M,M,M-configuration. However, there is no such structural arrangement in Pisomer 19. Therefore, M-isomer 20 contains four types of chirality elements: central, orientational, turbo and staircase chirality, which has not been documented in literature yet.