Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives

Faveri, Giorgio De; Ilyashenko, Gennadiy; Watkinson, Michael

doi:10.1039/c0cs00077a

Cited by 319 publications

(179 citation statements)

References 138 publications

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“…Hydrogen peroxide is a useful oxidant [1][2][3] in many different biocatalytic reactions [8,49,51,52,205]. However, it is also able to seriously damage the chemical structure of the proteins, inactivating enzymes.…”

Section: Discussionmentioning

confidence: 99%

Hydrogen Peroxide in Biocatalysis. A Dangerous Liaison

Hernández

Berenguer-Murcia²,

Rodrigues³

et al. 2012

COC

140

107

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Hydrogen peroxide is a substrate or side-product in many enzyme-catalyzed reactions. For example, it is a side-product of oxidases, resulting from the re-oxidation of FAD with molecular oxygen, and it is a substrate for peroxidases and other enzymes. However, hydrogen peroxide is able to chemically modify the peptide core of the enzymes it interacts with, and also to produce the oxidation of some cofactors and prostetic groups (e.g., the hemo group). Thus, the development of strategies that may permit to increase the stability of enzymes in the presence of this deleterious reagent is an interesting target. This enhancement in enzyme stability has been attempted following almost all available strategies: site-directed mutagenesis (eliminating the most reactive moieties), medium engineering (using stabilizers), immobilization and chemical modification (trying to generate hydrophobic environments surrounding the enzyme, to confer higher rigidity to the protein or to generate oxidation-resistant groups), or the use of systems capable of decomposing hydrogen peroxide under very mild conditions. If hydrogen peroxide is just a side-product, its immediate removal has been reported to be the best solution. In some cases, when hydrogen peroxide is the substrate and its decomposition is not a sensible solution, researchers coupled one enzyme generating hydrogen peroxide "in situ" to the target enzyme resulting in a continuous supply of this reagent at low concentrations thus preventing enzyme inactivation.This review will focus on the general role of hydrogen peroxide in biocatalysis, the main mechanisms of enzyme inactivation produced by this reactive and the different strategies used to prevent enzyme inactivation caused by this "dangerous liaison". Outlook

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Section: Discussionmentioning

confidence: 99%

Hydrogen Peroxide in Biocatalysis. A Dangerous Liaison

Hernández

Berenguer-Murcia²,

Rodrigues³

et al. 2012

COC

140

107

View full text Add to dashboard Cite

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“…They also studied various factors Optically active epoxides obtained from the catalytic enantioselective epoxidation of alkenes are important intermediates in asymmetric synthesis, since these compounds are very useful for the synthesis of chirons with up to two contiguous stereogenic centres [37,38]. Chiral epoxidation of allylic alcohols provides interesting building blocks for the asymmetric synthesis of biologically active compounds, and consequently, asymmetric epoxidation of allylic alcohols has been extensively developed [39].…”

Section: Epoxidationmentioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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Catalysis is a topic of continuous interest since it was discovered in chemistry centuries ago. Aiming at the advance of reactions for efficient processes, a number of approaches have been developed over the last 180 years, and more recently, porphyrins occupy an important role in this field. Porphyrins and metalloporphyrins are fascinating compounds which are involved in a number of synthetic transformations of great interest for industry and academy. The aim of this review is to cover the most recent progress in reactions catalysed by porphyrins in scalable procedures, thus presenting the state of the art in reactions of epoxidation, sulfoxidation, oxidation of alcohols to carbonyl compounds and C-H functionalization. In addition, the use of porphyrins as photocatalysts in continuous flow processes is covered.

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“…The main challenge for researchers has been to make the oxidation reaction the most chemo-, regio-and stereoselective. [116][117][118][119] Asymmetric epoxidation of alkenes using hydrogen peroxide as oxidant, has been a very active research field and has been investigated by many research groups. The most recent progress has been reviewed.…”

Section: Oxidation Of Alkenesmentioning

confidence: 99%

Synthetic utility of metal catalyzed hydrogen peroxide oxidation of C-H, C-C and C=C bonds in alkanes, arenes and alkenes: Recent advances

Wójtowicz‐Młochowska¹

2016

Arkivoc

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This review presents the current state of the art of homogenic and heterogenic oxygen transfer processes using hydrogen peroxide as oxygen source and compounds and complexes of tranisition metals, Fe, V, Cu, Mn, Rh, Mo, Ti, W, Pd, Os, Zr, Cr, Nb, Co, as the catalysts. Based on the reactions of C-H, C-C and C=C bonds in alkanes, arenes and alkenes various mechanisms of the oxygen-transfer processes are discussed and new methodologies for synthesis of alcohols, phenols, aldehydes, ketones, epoxides and carboxylic acids are indicated.

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Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives

Cited by 319 publications

References 138 publications

Hydrogen Peroxide in Biocatalysis. A Dangerous Liaison

Hydrogen Peroxide in Biocatalysis. A Dangerous Liaison

Porphyrins as Catalysts in Scalable Organic Reactions

Synthetic utility of metal catalyzed hydrogen peroxide oxidation of C-H, C-C and C=C bonds in alkanes, arenes and alkenes: Recent advances

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