Stereospecific positional alkene isomerization enables bidirectional central-to-axial chirality transfer.

ABSTRACT: Positional alkene isomerization is a powerful reaction for moving a C=C bond from one position to another. This transformation, as a high atom-economy and easy-to-handle process, has gained increasing prominence in both organic and material chemistry. Despite these advances, the stereospecific positional alkene isomerization to achieve bidirectional chirality transfer remains challenging. We report herein a bidirectional stereospecific positional alkene isomerization of chiral exocyclic alkene analogues by achiral Lewis base catalysis. By using this central-to-axial chirality transfer strategy, the axially chiral N-indolylquinolinones can be readily obtained from one configuration to two different configurations. Mechanistic studies indicated that the competitive alkene isomerization and M

SUBMITTER: Liu Q 

PROVIDER: S-EPMC12287271 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature