Quinoline
            <i>N</i>
            ‐Oxides

Jones, Gurnos; Baty, David J.

doi:10.1002/9780470187036.ch3

Cited by 2 publications

(2 citation statements)

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“…(2) Hydrogen bonds could be forming between the C-9 hydroxy group and the ester group. The p K a for quinoline N -oxide is 0.70, whereas the p K a for quinoline is 4.85 . In our opinion, when the quinoline nitrogen atom of cinchona alkaloid was oxidized, the hydrogen-bonding interactions between the C-9 hydroxy group and the ester group of 1a could be enhanced .…”

Section: Resultsmentioning

confidence: 67%

“…The pK a for quinoline N-oxide is 0.70, whereas the pK a for quinoline is 4.85. 21 In our opinion, when the quinoline nitrogen atom of cinchona alkaloid was oxidized, the hydrogen-bonding interactions between the C-9 hydroxy group and the ester group of 1a could be enhanced. 17c The stronger hydrogen bonding between N-oxide PTC and the substrate may be the reason for the high reactivity of the reaction.…”

Section: ■ Results and Discussionmentioning

confidence: 92%

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Enantioselective α-Benzoyloxylation of β-Keto Esters by N-Oxide Phase-Transfer Catalysts

et al. 2018

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An efficient and enantioselective α-benzoyloxylation of β-keto esters has been achieved by phase-transfer catalysis. This simple catalytic procedure is applicable to a range of β-keto esters with cinchona-derived N-oxide asymmetric phase-transfer catalysts and gives the corresponding products in good enantiopurity (up to 95% ee) and yield (up to 99%). This simple and effective oxyfunctionalization is a useful synthetic strategy for introducing an oxygen-containing functional group at the α position of β-dicarbonyl compounds.

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Section: Resultsmentioning

confidence: 67%

Section: ■ Results and Discussionmentioning

confidence: 92%