Selenium dioxide catalyzed oxidation of secondary amines with hydrogen peroxide. Simple synthesis of nitrones from secondary amines

Murahashi, Shun‐Ichi; Shiota, Tadashi

doi:10.1016/s0040-4039(00)96130-6

Cited by 184 publications

(49 citation statements)

References 9 publications

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“…Oxidation of secondary amines to nitrones is a method that, despite well documented with several oxidant systems (H 2 O 2 /SeO 2 , [13] Na 2 WO 4 , [14] oxaziridines, [15] H 2 O 2 or UHP/ Scheme 2.…”

Section: The Synthesis Of Nitronesmentioning

confidence: 99%

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Brandi

Cardona

Cicchi

et al. 2009

Chemistry A European J

236

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The synthesis of polyhydroxylated indolizidines and pyrrolizidines belonging to the class of iminosugars, endowed with a vast and assorted biological activity, can be achieved in a straightforward manner by a general strategy consisting of a highly stereoselective 1,3-dipolar cycloaddition of polyhydroxylated pyrroline-N-oxides followed by simple transformations of the isoxazolidine adducts. The strategy allows the complete control of the relative and absolute stereochemistry of the numerous stereogenic centers decorating these compounds.

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Section: The Synthesis Of Nitronesmentioning

confidence: 99%

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Brandi

Cardona

Cicchi

et al. 2009

Chemistry A European J

236

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“…Moreover diselenides can be easily oxidized in situ by hydrogen peroxide to seleninic acid or peroxyseleninic acid, which are in some cases excellent catalysts in the oxidation of organic compounds [21][22][23][24], as, for instance, epoxidation reaction of alkenes [25], Baeyer-Villiger reaction [26], oxidation of carbonyl compounds [27], dehydrogenation of carbonyl compounds [28][29], oxidation of secondary amines [30][31], oxidation of imines [32], or selenenylations or halogenations [33].…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

García-Marín

Toorn

Mayoral

et al. 2011

Journal of Molecular Catalysis A: Chemical

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A green strategy has been explored for olefin epoxidation which combines renewable solvents (derived from glycerol), aqueous hydrogen peroxide, and catalyst recycling (a seleninic acid derivative). The use of fluorinated glycerol derivatives allows good catalytic activity in the epoxidation of cyclooctene and cyclohexene with aqueous hydrogen peroxide, preventing epoxide hydrolysis to a great extent, which is particularly remarkable in the case of cyclohexene. Furthermore, recycling of the catalytically active phase is possible through distillation of the cyclohexene oxide from the reaction mixture, which can be subsequently recharged with fresh oxidant and substrate.

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“…Although the undesired C5 oxidation product 42 was eliminated, the conversion rate to yield the oxidation product (9 R )‐ 38 was slow. Other oxidation conditions involving SeO 2 26 or Me 3 ReO 3 ,27 resulted in the formation of complex mixtures (entries 4 and 5). Eventually, we found the addition of PbO 2 and AcOH after the oxidation of indoline (9 R )‐ 34 under conditions similar to those described in entry 1, provided N ‐oxoamidine (9 R )‐ 38 in 81 % yield in one pot (entry 6).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework

Yamada

Ideguchi-Matsushita

Hirose

et al. 2015

Chemistry A European J

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The total synthesis of the indole alkaloids, neoxaline, oxaline and meleagrin A, all containing a unique indoline spiroaminal framework, was accomplished through the stereoselective introduction of a reverse prenyl group to the congested benzylic carbon of furoindoline, a two-pot transformation of indoline (containing three nitrogen atoms at appropriate positions) to the featured indoline spiroaminal framework, and elimination of carbonate assisted by the adjacent imidazole moiety to construct the (E)-dehydrohistidine. The absolute stereochemistry of neoxaline was elucidated through our total synthesis. In addition, we evaluated the bioactivity, especially the anti-infectious properties, of neoxaline and oxaline, and of some synthetic intermediates.

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Selenium dioxide catalyzed oxidation of secondary amines with hydrogen peroxide. Simple synthesis of nitrones from secondary amines

Cited by 184 publications

References 9 publications

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework

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