Herein we reported novel lead-free 2D chiral perovskites, namely (R/S-ClMBA)2SnI4. The crystal structure investigation confirmed the crystallization in non-centrosymmetric space groups for the R-and S-enantiomers, opposite to the racemic compound. The presence of chiral ligands effectively induces the emergence of chiroptical properties, as demonstrated by the CD spectra. The optical properties determination by UV-vis spectroscopy and PL shows a direct band gap of about 2.12 eV for the two chiral perovskites and 2.08 for the racemic compound with a broad emission centered around 1.70 eV. DFT calculation confirms Rashba band splitting, with the highest spin splitting values of 17.8 and 18.7 meV for the R-and S-isomer, respectively, and without any splitting for the racemic composition, thus confirming the structural distortion induced by chiral organic cations. Such structural distortions eventually lead to the formation of STEs and concomitant redshifted emission. Thanks to the reported data on this new system, some preliminary attempts to correlate chiroptical properties to structural distortions and the nature of the central metal are proposed.