Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.
Chirag D GheewalaJennifer S HirschiWai-Hang LeeDaniel W PaleyMathew J VetticattTristan H LambertPublished in: Journal of the American Chemical Society (2018)
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.
Keyphrases
- ionic liquid
- electron transfer
- room temperature
- electron microscopy
- quantum dots
- capillary electrophoresis
- high glucose
- aqueous solution
- diabetic rats
- solar cells
- high resolution
- water soluble
- drug induced
- dual energy
- mass spectrometry
- oxidative stress
- endothelial cells
- magnetic resonance imaging
- magnetic resonance
- solid state