Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions.

ABSTRACT: Despite the rapid development of asymmetric synthesis, judging the remoteness of stereocontrol has remained an intuitive and empirical practice, particularly for reactions that create non-central chirality. We put forward a stereocontrol connectivity index to parameterize asymmetric reactions according to the bond connectivity relationships between the prochiral stereogenic elements, the reactive sites, and the stereochemical-defining substituents. The indices can be generated based on analysis of the chemical structures of the starting materials and products, without mechanistic insights of the transformation. Representative examples of reactions that establish point chirality, axial chirality, planar chirality, and "inherent chirality" are illustrated using the stereocontrol connectivity

SUBMITTER: On IKW 

PROVIDER: S-EPMC12498253 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature