Ground state reactant and transition state geometries for dimethyl malonate Michael addition reactions were built using Schrödinger’s R-Group Enumeration. R-groups were placed on various different positions of the Michael acceptor; the position depended upon the molecules in question. All structures were built in Gaussian16 (Revisions A.03 and C.01) and were conformationally searched using Schrödinger’s MacroModel (version 12.7). All structures were subsequently optimised using Gaussian16 (Revisions A.03 and C.01) using AM1 and wB97X-D/def2-TZVP (IEFPCM=Water)//wB97X-D/def2-TZVP. 
For distortion/interaction-activation strain calculations, python code (available on the associated GitHub page: https://github.com/the-grayson-group/distortion-interaction_ML) was used to separate the distorted reactant structures before single point energies were calculated using Gaussian16 (Revision C.01) using AM1 and the DFT level of theory used in the original transition structure calculation.