Let us then proceed with the calculation of stabilization energy of the two chiral isomers of the TS in the presence of the 2D-LEF. For this purpose, we employ the following relationship: reveals that the TS1(R) is better aligned than TS1(S) in the direction of the LEF, and it possesses relatively higher dipole moments along the y-and z-axes. As such, this dipole moment of TS1(R) will interact more strongly with the LEF than TS1(S), which possesses a lower z-LEF and higher y-EEF which is misoriented and destabilizes this TS. As such, the pro-S TS is less stabilized compared with the pro-R TS. The interaction energy calculations predict that the two directional electric fields complement each other for the reactivity and the selectivity. Clearly therefore, the LEF of the system is the decisive factor for the exclusive Rselective pathway and for its enhanced reactivity. This was further supported by a separate calculation, in which we stripped the cage and charged substitution, and found no enantioselectivity (see SI, Figure ).