Divergent Oxidation Reactions of E‐ and Z‐Allylic Primary Alcohols by an Unspecific Peroxygenase Article Swipe
Gideon Grogan
,
Jiacheng Li
,
Cristina Duran
,
Balázs Pogrányi
,
Katy A. S. Cornish
,
Jared Cartwright
,
Sílvia Osuna
,
William P. Unsworth
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1002/ange.202422241
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1002/ange.202422241
Unspecific peroxygenases (UPOs) catalyze the selective oxygenation of organic substrates using only hydrogen peroxide as the external oxidant. The PaDa−I variant of the UPO from Agrocybe aegerita catalyses the oxidation of Z ‐ and E ‐allylic alcohols with complementary selectivity, giving epoxide and carboxylic acid/aldehyde products respectively. Both reactions can be performed on preparative scale with isolated yields up to 80 %, and the epoxidations proceed with excellent enantioselectivity (>99 % ee ). The divergent reactions can also be used to transform E / Z mixtures of allylic alcohols, enabling both product series to be isolated from a single reaction. The utility of the epoxidation method is exemplified in the total synthesis of both enantiomers of the insect pheromone disparlure, including a highly enantioselective gram‐scale transformation. These reactions provide further evidence for the potential of UPOs as catalysts for the scalable preparation of important oxygenated intermediates.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/ange.202422241
- OA Status
- hybrid
- References
- 121
- Related Works
- 10
- OpenAlex ID
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https://openalex.org/W4405244259Canonical identifier for this work in OpenAlex
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https://doi.org/10.1002/ange.202422241Digital Object Identifier
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Divergent Oxidation Reactions of E‐ and Z‐Allylic Primary Alcohols by an Unspecific PeroxygenaseWork title
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articleOpenAlex work type
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enPrimary language
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2024Year of publication
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2024-12-10Full publication date if available
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Gideon Grogan, Jiacheng Li, Cristina Duran, Balázs Pogrányi, Katy A. S. Cornish, Jared Cartwright, Sílvia Osuna, William P. UnsworthList of authors in order
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https://doi.org/10.1002/ange.202422241Publisher landing page
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hybridOpen access status per OpenAlex
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https://doi.org/10.1002/ange.202422241Direct OA link when available
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Allylic rearrangement, Chemistry, Aldehyde, Hydrogen peroxide, Epoxide, Selectivity, Enantiomer, Catalysis, Combinatorial chemistry, Chemoselectivity, Enantioselective synthesis, Organic chemistryTop concepts (fields/topics) attached by OpenAlex
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0Total citation count in OpenAlex
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