Biocatalytic Single‐Step Alkene Cleavage from Aryl Alkenes: An Enzymatic Equivalent to Reductive Ozonization

Mang, Harald; Gross, Johannes; Lara, Miguel; Goessler, Christian; Schoemaker, Hans E.; Guebitz, Georg M.; Kroutil, Wolfgang

doi:10.1002/anie.200601574

Cited by 48 publications

(16 citation statements)

References 56 publications

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“…In 2006, Kroutil and co-workers reported that aM n IIIdependent enzyme from Trametes hirsuta (AlkCE) is able to oxidatively cleave C=Cd ouble bonds,y ielding the corresponding aldehydes or ketones (Scheme 26). [99] Scheme 20. Most common biocatalyticepoxidation methods employing monooxygenases, [80] peroxygenases, [81] or lipases in the "perhydrolase" approach and some representative products.…”

Section: Ozonolysis Of Alkenes To Aldehydesmentioning

confidence: 99%

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Biocatalytic Oxidation Reactions: A Chemist's Perspective

et al. 2018

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Oxidation chemistry using enzymes is approaching maturity and practical applicability in organic synthesis. Oxidoreductases (enzymes catalysing redox reactions) enable chemists to perform highly selective and efficient transformations ranging from simple alcohol oxidations to stereoselective halogenations of non‐activated C−H bonds. For many of these reactions, no “classical” chemical counterpart is known. Hence oxidoreductases open up shorter synthesis routes based on a more direct access to the target products. The generally very mild reaction conditions may also reduce the environmental impact of biocatalytic reactions compared to classical counterparts. In this Review, we critically summarise the most important recent developments in the field of biocatalytic oxidation chemistry and identify the most pressing bottlenecks as well as promising solutions.

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Section: Ozonolysis Of Alkenes To Aldehydesmentioning

confidence: 99%

“…Aerobic cleavage of styrenes with AlkCE from Trametes hirsuta. [99] Scheme 27. Use of an engineered P450 monooxygenase (aMOx) to catalyse the anti-Markovnikov Wacker-Tsuji oxidation of alkenes.…”

Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Biocatalytic Oxidation Reactions: A Chemist's Perspective

et al. 2018

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“…Furthermore, neither corresponding epoxide nor diol was detected during the reaction course leaving out the possibility of these as intermediates in a possible pathway. Moreover, the inability of culture supernate to convert t-anethole epoxide into the corresponding aldehyde hinted out that the alkene cleavage is a one step mechanism employing molecular oxygen as oxidant [26]. Further, the culture supernate was found positive for the catalase activity.…”

Section: Proposed Mechanismmentioning

confidence: 96%

“…A number of biocatalytic reports are available for the synthesis of carbonyls either by oxidation of alcohols [21][22][23][24] or by oxidative alkene cleavage [25][26][27]. Still, the development of chemoselective methods that efficiently discriminate among various functional groups remains challenging.…”

Section: Introductionmentioning

confidence: 99%

A Synergic Blend of Newly Isolated Pseudomonas mandelii KJLPB5 and [hmim]Br for Chemoselective 2° Aryl Alcohol Oxidation in H2O2: Synthesis of Aryl Ketone or Aldehydes via Sequential Dehydration-Oxidative C=C Cleavage

Sharma

Salwan

et al. 2011

Catal Lett

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Pseudomonas mandelii KJLPB5 is reported for the oxidation of aryl alcohols in ionic liquid [hmim]Br (1-hexyl-3-methyl imidazolium bromide) with H 2 O 2 . With a slight alteration of reaction conditions, the developed protocol leads either to (i) chemoselective oxidation of 2°a ryl alcohols over 1°and aliphatic counterparts or (ii) direct one pot-two step sequential conversion of 2°aryl alcohols into corresponding one or two carbons shorter aryl aldehydes through oxidative cleavage pathway, thus providing a new facet to metal-free oxidations. The key operational parameters such as substrate concentration, incubation temperature, incubation time, ionic liquid type and ionic liquid concentration are also optimized.

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“…In accordance with the literature [27], the dialdehyde 1b can be obtained from the 1,2-diol 1d with lead tetraacetate. Oxidative cleavage of carbon-carbon double bonds to carbonyl compounds is also a very frequently used method in synthetic organic chemistry [37,[39][40][41][42].…”

Section: Oxidation Of 1h-indenementioning

confidence: 99%

Transition Metal Substituted Polyoxotungstates in the Catalytic Oxidation of 1H-Indene and 1,2-Dihydronaphthalene with Hydrogen Peroxide

et al. 2008

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The oxidation of 1H-indene and 1,2-dihydronaphthalene with hydrogen peroxide in the presence of Mn(III) or Fe(III) substituted Keggin-type polyoxotungstates is described. The products obtained depend on the catalyst and reaction conditions. Ring cleavage was observed, affording dialdehydes under mild and environmentally friendly conditions. Other main products were the a-hydroxy-ketones. The resulting epoxides seem to be intermediates to other oxygenated products.

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Biocatalytic Single‐Step Alkene Cleavage from Aryl Alkenes: An Enzymatic Equivalent to Reductive Ozonization

Cited by 48 publications

References 56 publications

Biocatalytic Oxidation Reactions: A Chemist's Perspective

Biocatalytic Oxidation Reactions: A Chemist's Perspective

A Synergic Blend of Newly Isolated Pseudomonas mandelii KJLPB5 and [hmim]Br for Chemoselective 2° Aryl Alcohol Oxidation in H2O2: Synthesis of Aryl Ketone or Aldehydes via Sequential Dehydration-Oxidative C=C Cleavage

Transition Metal Substituted Polyoxotungstates in the Catalytic Oxidation of 1H-Indene and 1,2-Dihydronaphthalene with Hydrogen Peroxide

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