1283098-40-7

Upstream product

• 327022-92-4 1-pentafluorophenyl-3-buten-1-ol 
• 1283098-36-1 1-(perfluorophenyl)butane-1,4-diol 
• 1283098-37-2 4-oxo-4-(2,3,4,5,6-pentafluorophenyl)butanal 
• 1283098-38-3 (1R,2R)-2-(2-(2,3,4,5,6-pentafluorophenyl)-1H-pyrrol-1-yl)cyclohexanamine 
• 1325215-45-9 C₂₅H₂₂F₅N₃O₂S 
• 1283098-39-4 C₄₁H₃₅F₁₀N₅O₂ 
• 653-37-2 perfluorobenzaldehyde 

Relevant academic research and scientific papers

Transition-state charge stabilization through multiple non-covalent interactions in the guanidinium-catalyzed enantioselective claisen rearrangement

The mechanism by which chiral arylpyrrole-substituted guanidinium ions promote the Claisen rearrangement of O-allyl α-ketoesters and induce enantioselectivity was investigated by experimental and computational methods. In addition to stabilization of the developing negative charge on the oxallyl fragment of the rearrangement transition state by hydrogen-bond donation, evidence was obtained for a secondary attractive interaction between the π-system of a catalyst aromatic substituent and the cationic allyl fragment. Across a series of substituted arylpyrrole derivatives, enantioselectivity was observed to vary predictably according to this proposal. This mechanistic analysis led to the development of a new p-dimethylaminophenyl-substituted catalyst, which afforded improvements in enantioselectivity relative to the parent phenyl catalyst for a representative set of substrates.