Next, the challenging double enantioinduction with 1-alkynyl indoles was envisaged to furnish valuable atropoisomers featuring two different chiral C-N. To address the challenging annulation process, we proposed utilizing a developed an MVRL model to disclose the key features responsible in atropo-selectivity and prediction with the best performing ligand from the introduced chiral oxazolines. We identified the key attributes needed to effectively describe chiral oxazoline ligands. To do this, we implemented a general computational workflow (Scheme 4B) designed to extract various descriptors at three distinct stages: (1) the ligand in its free state (preligand) (FL), (2) the ligand coordinated with cobalt(III) in its cyclometalated complex state (CMC), and (3) at the fragmented state derived from the cyclometalated complex, used to compute the interaction energy (IE). Neutral preligand states were considered from the ligand screening data for descriptor calculation and selectivity modeling. The workflow began with the generation of 3D ligand structures from SMILES strings using the ETKDG method. Next, a conformational search was performed within a 6 kcal mol -1 energy window using the GFN2-xTB-based CREST tool. The lowest-energy conformer identified through this process was then optimized and further refined with density functional theory (DFT) to limit computational costs. All features at every stage were obtained from the DFT-refined structures (see Supporting Information for complete details). To compare the urea and thiourea ligands against amide and enol derivatives, principal component analyses (PCA) were performed using all the acquired 36 descriptors. The third principal component (PC) was able to well separate all classes. Later the deconstructed PC analysis with the free ligand descriptors revealed the electronic features as the key distinguisher among the other feature types (see Supporting Information for details).