Both the examples that follow require a representation for the relative stereoconfiguration of
stereogenic centers. They also require the ability to assign the stereoconfiguration of individual
stereogenic centers.
Example: non-stereoselective reduction
As an example, consider the reaction shown in Figure 1. The reactant contains four stereogenic
centers of known absolute configuration. The keto group is reduced to the alcohol using a nonstereoselective
procedure. This introduces a new stereogenic center, which can adopt either the
R or S configuration. The sample, therefore, is a mixture of the two diastereomers (epimers). This
transformation does not affect the stereochemical configuration of the stereogenic centers on the
cyclopentane ring.