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- W3211913810 abstract "A sterically strained ionic Brønsted pair complex obtained from a sterically bulky base 2,4,6-tri-tert-butylpyridine and hydrochloric acid imbues unusual reactivity to the anionic chloride. The complete shielding of the cationic [N-H]+ by the bulky ortho-tert-butyl groups weakens the possible hydrogen-bonding interactions with the chloride anion, and the [N-H]+···Cl- distance is unusually longer (3.10 Å). This results in strained/frustrated electrostatic interactions between the ion-pair, thus infusing an increased reactivity in both of the ions, which results in the activation of a third molecule like thiol via hydrogen-bonding. This intriguing weak interaction-based reactivity has been utilized to develop an organocatalytic synthesis of 2-deoxy-β-thioglycosides from glycals. While the 1H NMR studies showcase the diamagnetic activation of thiols in the presence of the catalyst, the electron paramagnetic resonance (EPR) studies reveal the generation of a radical species that suggests a possible frustrated radical pair catalysis. Besides, IR spectroscopic studies explain the intriguing influence of size/charge density of the anion on the solvation-insusceptible, cationic [TTBPyH]+ and on the observed reactivity." @default.
- W3211913810 created "2021-11-22" @default.
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- W3211913810 date "2021-11-18" @default.
- W3211913810 modified "2023-09-27" @default.
- W3211913810 title "Sterically Strained Brønsted Pair Catalysis by Bulky Pyridinium Salts: Direct Stereoselective Synthesis of 2-Deoxy and 2,6-Dideoxy-β-thioglycosides from Glycals" @default.
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- W3211913810 doi "https://doi.org/10.1021/acs.joc.1c02305" @default.
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