The reduction of hindered chiral ketones with sodium borohydride can be analyzed by GC and polarimetry and has been revealed to be a straightforward laboratory experiment for undergraduate students to obtain contact with stereoselective reactions. The characteristic feature of this reaction, consisting in the formation of two diastereomers, is the possibility of determining the percentage of each isomer formed by GC analysis and by polarimetry using the values of the specific rotation of the mixture and the specific rotations of the pure isomers.
Serra et al. (Wed,) studied this question.