The geometry of each of the chiral modifier/substrate complexes was optimized using DFT calculations and a BLYP functional. The theoretical enantiomeric excess was calculated from the energy of each of the proposed complexes. The calculations were carried out considering different reaction solvents through the use of COSMO program.
It was found that this simple model allows predicting the experimental values of both the sense of enantiodifferentiation and the enantiomeric excess with a good approximation. It was also able to predict the inversion of configuration when using the (S)-(+)-1-aminoindane as chiral modifier in polar solvents such as acetic acid and 2-propanol.