Computing organic stereoselectivity is now a standard part of synthetic and mechanistic chemistry. In general, either the pathway with the lowest energy transition state leads to the preferred product, or else the thermodynamically favourable product is formed. However, there are also reactions where the product selectivity is strongly influenced by reaction dynamics. In these cases, calculation of TS energies by itself is not enough to understand the outcome. Such reactions tend to have bifurcating reaction surfaces or involve processes with a shallow intermediate that connects two transition states (TS), where the first TS is much higher in energy than the second one (Figure ). The role of reaction dynamics has been largely overlooked, with computational organic chemists usually focusing on other factors, such as kinetics, through utilizing the Transition State Theory (TST). One possible reason might be the high computational cost. Traditionally, expensive molecular dynamics (MD) simulations need to be run to produce a large number of reaction trajectories to confirm the effect of reaction dynamics. Thus, most of the reported examples of dynamically controlled reactions tend to be simple systems involving only a few atoms. Perhaps as a result of this, synthetic chemists may well assume that this type of selectivity is of no practical relevance to experimental organic chemistry. In this paper, we demonstrate that the selectivity in a 'normal' organic reaction cannot be reproduced by TST and can be explained through dynamic control. Recently, we developed an algorithm, VRAI-selectivity, to analyse and predict selectivity outcomes of dynamically controlled reactions straightforwardly without expensive computations. In this study, we use VRAI-selectivity calculations to investigate a set of complex organic reactions reported by Ryu et al. (Figure ) and demonstrate that their selectivity is heavily influenced by reaction dynamics. The reactions are catalysed by chiral oxazaborolidinium ion (COBI) catalysts, a well-established and versatile catalyst system developed by Corey et al. COBI catalysts effectively actives carbonyl group as a Lewis acid and thus have broad applicability in various organic reactions under research setting. Our study initially centres around the ketone selective reactions (Figure .B). These reactions involve identical substrates but exhibit distinct chemo-and stereoselective outcomes due to subtle variations in the substituents on the aromatic rings of the catalysts. We show that reaction dynamics plays a key role in determining the selectivity outcome. To validate this finding, we further selected two additional reactions: the epoxide 12 and aldehyde 13 selective reaction (Figure .C and D), in which the main products are epoxide and aldehyde, respectively. Despite changes in the substituents of diazo and aldehyde substrates, the underlying mechanism remains the same and the reaction outcomes are also governed by reaction dynamics. . We investigated the above reaction systems in this project. All enantiomeric excess (ee) values above are determined from chiral HPLC. For the ketone 14 and aldehyde 13 selective reaction, the major to minor product ratio comes directly from the crude product 1 H NMR. For the epoxide selective reaction, the yield for the aldehyde has not been explicitly reported for this reaction. We assume that the loss in percentage yield of the epoxide is all attributed to the aldehyde by-product. The major to minor product ratio is estimated from percentage yield of the isolated SR epoxide and diastereomeric ratio, which comes from 1 H NMR of the crude product. Ryu et al. reported that changing the diazo substituent from CO2 t Bu to CO2Me do not alter the experimental outcome significantly. Thus, we simplified the diazo substituent from CO2 t Bu to CO2Me for the computational investigation.