Oxyfunctionalization of hydrocarbons. 1. Protolytic cleavage-rearrangement reactions of tertiary alkyl hydroperoxides with magic acid

Oláh, George A.; Parker, David G.; Yoneda, Norihiko; Pelizza, Franco

doi:10.1021/ja00424a038

Cited by 45 publications

(23 citation statements)

References 5 publications

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“… 33 The most common method for observing the cation is using a superacid solvent at low temperature. 34 Even in these instances, the most commonly reported species were tertiary cations or dioxocarbenium cations. In 2009, Yoshida and co-workers described the low-temperature observation of a pyranose-derived oxocarbenium cation in CH 2 Cl 2 using electrochemical oxidation (the cation pool method).…”

Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.

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Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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“…For example, 9g showed an absorption band at 3298 cm −1 in the IR spectrum corresponding to the OH group and a singlet at δ 4.88 ppm in the 1 H-NMR spectrum due to the OH group. In the 13 C-NMR spectrum, the quaternary carbon C-4 bearing the OH group appeared at δ 75.8 ppm and this is significantly different from that having the OOH group ( Table 6 ) [ 72 ]. In addition, the elemental analysis of 9g supported the molecular formula of C 22 H 18 N 2 O 3 .…”

Section: Resultsmentioning

confidence: 99%

Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds

et al. 2011

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The Mn(III)-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols. The synthesis of 30 heterocyclic 1,3-dicarbonyl compounds, the corresponding hydroperoxides and the 10 alcohols, their characterization, and the limitations of the procedure are described. In addition, the mechanism of the hydroperoxidation and the redox decomposition of the hydroperoxides are discussed.

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“…603 Similarly, Baeyer-Villiger oxidation of several ketones in the presence of H 2 O 2 and superacids gave similar product compositions. 603 Similarly, Baeyer-Villiger oxidation of several ketones in the presence of H 2 O 2 and superacids gave similar product compositions.…”

Section: ð5:214þmentioning

confidence: 88%