Ivan Keng Wee On, Yu Kun Choo, Sambhav Baid, Ye Zhu
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Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions.
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 index produced following a unified 3-step process. Application of such stereochemical classification could facilitate the development of new synthetic methodologies and catalyst systems to construct diverse chiral molecules.
期刊介绍:
The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
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