Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols.

ABSTRACT: Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectively edited without further structural modification, a strategy with the potential to allow new classes of late-stage stereochemical manipulation and provide access to rare or valuable stereochemical configurations. In this work, we describe a selective epimerization of cyclic diols enabled by hydrogen atom transfer photocatalysis and boronic acid mediated transient thermodynamic control, selectively generating less stable cis products from the otherwise favored trans isomers. A range of substitution patterns and ring sizes are

SUBMITTER: Oswood CJ 

PROVIDER: S-EPMC9676085 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature