TEMPO-Catalyzed Oxidation of 3-<i>O</i>-Benzylated/Silylated Glycals to the Corresponding Enones Using a PIFA–Water Reagent System

Chennaiah, Ande; Verma, Ashish; Vankar, Yashwànt D.

doi:10.1021/acs.joc.8b01191

Cited by 21 publications

(13 citation statements)

References 40 publications

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“…Compound 36 was synthesized from (((2 R ,3 R ,4 R )-3-(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2 H -pyran-4-yl)oxy)( tert -butyl)dimethylsilane (300 mg, 0.68 mmol) by following general procedure A. Overall yield: 84%, 342.0 mg. R f : 0.5 (5% EtOAc/hexane).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Hexenuloses and a Library of Disaccharides Possessing 3-oxo-glycal Unit

2022

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An expeditious method for the synthesis of monosaccharides and disaccharides possessing 3-oxo-glycal units is revealed. Several monosaccharides and disaccharide-derived glycals are converted to the corresponding hexenuloses in three steps involving halo-alkoxylation, dehydrohalogenation, and ketalyzation reactions. A number of 3-oxo-glycals are synthesized to show the methodology's importance and generality. Further, the protocol is successfully applied to synthesize a rare-sugar disaccharide donor unit present as part of the trisaccharide moiety in the reported natural product, versipelostatin.

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Section: Methodsmentioning

confidence: 99%

“…Due to its high importance and applicability, the development of synthetic routes for the preparation of 3-oxo-glycals is in demand. There are a few reports to synthesize hexenuloses . However, most reported methods suffer from poor yield, demand anhydrous conditions, and lack reproducibility.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Hexenuloses and a Library of Disaccharides Possessing 3-oxo-glycal Unit

2022

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“…Various scientific papers, book chapters, and review articles have been published on the chemistry of hypervalent iodine. [10][11][12][13][14][15][16][17][18]. The functionalization of carbonyl compounds [19,20], cyclization [21][22][23][24], oxidative rearrangements [25][26][27], alkene difunctionalizations [28][29][30][31], and atom-transfer reactions [32], in the presence of hypervalent iodine compounds as reagents or catalysts, is now well established.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

et al. 2022

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The chemistry of polyvalent iodine compounds has piqued the interest of researchers due to their role as important and flexible reagents in synthetic organic chemistry, resulting in a broad variety of useful organic molecules. These chemicals have potential uses in various functionalization procedures due to their non-toxic and environmentally friendly properties. As they are also strong electrophiles and potent oxidizing agents, the use of hypervalent iodine reagents in palladium-catalyzed transformations has received a lot of attention in recent years. Extensive research has been conducted on the subject of C—H bond functionalization by Pd catalysis with hypervalent iodine reagents as oxidants. Furthermore, the iodine(III) reagent is now often used as an arylating agent in Pd-catalyzed C—H arylation or Heck-type cross-coupling processes. In this article, the recent advances in palladium-catalyzed oxidative cross-coupling reactions employing hypervalent iodine reagents are reviewed in detail.

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“…5 Owing to its unique oxidation mechanism as a nitroxyl radical catalyst, we envisaged that 1 might also be an effective oxidation catalyst for electron-rich benzylic ethers such as p-methoxybenzyl (PMB) ethers (Scheme 1). 6 The PMB group has been widely used as a protecting group for alcohols, 7 as it can be easily introduced via various methods 8 and removed using common oxidizing agents. For the oxidative deprotection of PMB ethers, stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) 9 or more than 2 equiv of ceric ammonium nitrate (CAN) 10 are usually employed, although various other methods have been reported.…”

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confidence: 99%

Chemoselective Oxidation ofp-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst

et al. 2020

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The oxidation of p-methoxy benzyl (PMB) ethers was achieved using nitroxyl radical catalyst 1, which contains electron-withdrawing ester groups adjacent to the nitroxyl group. The oxidative deprotection of the PMB moieties on the hydroxy groups was observed upon treatment of 1 with 1 equiv of the co-oxidant phenyl iodonium bis(trifluoroacetate) (PIFA). The corresponding carbonyl compounds were obtained by treating the PMB-protected alcohols with 1 and an excess of PIFA.

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TEMPO-Catalyzed Oxidation of 3-O-Benzylated/Silylated Glycals to the Corresponding Enones Using a PIFA–Water Reagent System

Cited by 21 publications

References 40 publications

Synthesis of Hexenuloses and a Library of Disaccharides Possessing 3-oxo-glycal Unit

Synthesis of Hexenuloses and a Library of Disaccharides Possessing 3-oxo-glycal Unit

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Chemoselective Oxidation ofp-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst

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