Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Bronsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

ABSTRACT: An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.

SUBMITTER: Gheewala CD 

PROVIDER: S-EPMC5859540 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature