Fig. 3: Rate-determining nucleophilic attack TS structures and the visualization of the NCI surfaces.
From: Catalytic enantioselective nucleophilic desymmetrization of phosphonate esters
a, Three-dimensional structures of TS1-(R) for the formation of the (R)-product. b, Three-dimensional structures of TS1-(S) for the formation of the (S)-product. Bond lengths of the TS geometries are given in Å. NCI surfaces are represented as the coloured regions in the figure. Multiple stabilising inter- and intra-molecular NCIs such as hydrogen bonding, π–π and CH–π interactions are observed in the favoured TS TS1-(R), while the destabilizing steric repulsion between the substrate, nucleophile and catalyst exists in the unfavoured TS TS1-(S).
