Control of dynamic sp³-C stereochemistry.

ABSTRACT: Stereogenic sp³-hybridized carbon centres are fundamental building blocks of chiral molecules. Unlike dynamic stereogenic motifs, such as sp³-nitrogen centres or atropisomeric biaryls, sp³-carbon centres are usually fixed, requiring intermolecular reactions to undergo configurational changes. Here we report the internal enantiomerization of fluxional carbon cages and the consequences of their adaptive configurations for the transmission of stereochemical information. The sp³-carbon stereochemistry of the rigid tricyclic cages is inverted through strain-assisted Cope rearrangements, emulating the low-barrier configurational dynamics typical for sp³-nitrogen inversion or conformational isomerism. This dynamic enantiomerization can be sto

SUBMITTER: Bismillah AN 

PROVIDER: S-EPMC10159849 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature