Predicting "realistic" compounds of given chemical reactions with virtual synthesis tools usually requires the manual intervention of experienced chemists in the enumeration phase for the selection of appropriate reactants, assignment of the corresponding reaction sites, and removal of the unlikely products. To automate the virtual synthesis process, we have moved the expertise intensive parts from the compound library design phase to the reaction library design phase. ChemAxon is building an in silico reaction library containing important preparative transformations, where each reaction definition contains a generic transformation scheme and additional rules to handle the various starting compounds according to the corresponding chemo-, regio-, and stereoselectivity issues. Having well designed reaction definitions in hand, our software tool is able to generate synthetically feasible compound libraries with minimal effort in the enumeration phase.