An important aspect about model development is its transferability to outof-set reaction components, and most importantly the application of the model for a synthesis project. The work by Betinol et al., exemplifies this scenario, by demonstrating how previously developed statistical models can be extrapolated to structurally diverse substrates. Four goals were set at the onset of this research project: 1) application of an existing model to the synthesis of complex scaffolds; 2) application to the synthesis of a natural product; 3) preferred catalyst for a given reaction; 4) preferred route (reaction type) for the synthesis of a given product. For Goal #1 Betinol et al. investigated the CPA catalyzed nucleophilic addition to iminiums. The model was tested on three reported reactions for the functionalization of indoles (as relevant scaffolds for biological compounds) that are catalyzed by CPAs.