Statistical models were pursued for regioselectivity of the hydroformylation reaction (e.g., formation of aldehyde 6 vs 7) by evaluating the data with greater than 20% conversion (the same reactivity threshold as was used in the logistic regression model). An additional curation step was found necessary to produce statistically robust linear models based on the hypothesis that disparate ligand types may impart selectivity through unique mechanisms. As the training set was diverse, interrogation of the chemical space revealed a group of ligands which occupied a position in chemical space remote from the remainder of the ligands evaluated (see SI Fig. ). This included examples of several phosphite ligands that were removed from the training set resulting in a robust two-term model for regioselectivity using an electronic parameter P-C σ occupancy and a steric parameter %Vbur NE (Fig. ). The use of the chemical space map is noteworthy as it provided a method to visualize and curate the dataset. As the ultimate step in the workflow, virtual screening of the entire bisphosphine database was applied to identify ligands that were first predicted to be "active" and then predicted to be selective from the classification and linear regression models, respectively. A number of readily accessible ligands were selected and tested experimentally with both extrapolations and interpolations included to gauge model robustness (vide infra). For the Hayashi-Heck reaction, HexaMeO-BIPHEP 21 L12 was found to result in superb reaction performance and provided the desired product 4 in a regioisomeric ratio of 98.6:1.4 consistent with the predicted outcome (98:2). This represents a ~1 kcal/mol extrapolation in regioselectivity relative to the previous optimal ligand, Segphos L5. The reaction also resulted in an enantiomeric ratio of 93:7 (predicted 95:5), and 100% conversion. The multi-objective workflow was also highly successful in identifying a significantly improved ligand for the hydroformylation with Walphos L13 furnishing (R,S)-6 with an exceptional regioisomeric ratio of 99.1:0.9 (predicted 98:2), and 100% conversion. L13 also provides ~1 kcal/mol improvement in regioselectivity relative to (R,R)-Ph-BPE L6, the previousbest ligand. These significant improvements could be realized on gram scale with the first step providing (R)-4 in 77% isolated yield with 98:2 rr and 93.5:6.5 er and the second providing (R,S)-6 with 99:1 rr and 97:3 dr (Fig. ). Owing to its lability, (R,S)-6 was directly converted to the corresponding stable oxime (R,S)-8 in 71% isolated yield over two steps. In addition to producing the desired product in high yield, these superior catalysts provided regio-and stereochemical purity high enough to obviate extensive purification thus streamlining the route towards API 1.