Preparation of chiral diols by the osmium-catalysed, indirect anodic oxidation of olefins

Amundsen, Alan R.; Balko, E. N.

doi:10.1007/bf01023722

Cited by 33 publications

(21 citation statements)

References 10 publications

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“…Applications of mediated processes can span the whole range of synthetic chemistry and two examples will be given in Scheme where inorganic as well as organic redox catalysts are applied to regenerate chiral transition metal catalyst as well as chiral biocatalysts (HLADH=horse liver alcohol dehydrogenase) …”

Section: Direct Versus Indirect Electrolysismentioning

confidence: 99%

Basic Strategies and Types of Applications in Organic Electrochemistry

2019

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Dedicated to one of my heroes in organic electrochemistry; the late Prof. Jun-ichi YoshidaThe outlook of this paper is to give a short overview of the basic requirements to perform electro-organic transformations. The aim is to explain the strategies and possible applications in organic electrochemistry as simply as possible and is directed to those scientists who are not necessarily trained electrochemists and those that intend to utilize this powerful and, nowadays, very popular tool in their research. Different types of electrolysis performed in a galvanostatic/potentiostatic/alternating current fashion will be presented and the strategies to perform divided/undivided/quasi-divided electrolysis will be covered. The application of direct/indirect/cation-pool electrolysis as well as several variants of paired electrolysis will be briefly explained utilizing selected examples.

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Section: Direct Versus Indirect Electrolysismentioning

confidence: 99%

Basic Strategies and Types of Applications in Organic Electrochemistry

2019

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“…In the original Sharpless procedure, 3 equivalents of the ferricyanide salt were added to enable good turnover for the asymmetric dihydroxylation with excellent ee's. Making use of anodic regeneration, Amundsen and Balko were able to reduce the stoichiometry to 0.4 equivalents using coupled redox cycles ( Figure 3) in a divided cell with Pt electrodes at constant potential [67]. Similar to the Sharpless protocol, the authors used a biphasic mixture with the Fe salt in the aqueous phase and the organic transformation occurring in the organic phase, with re-oxidation of the Os catalyst taking place at the solvent interface.…”

Section: Alkene Functionalizationmentioning

confidence: 99%

Recent Advances in Asymmetric Catalytic Electrosynthesis

Margarita

Lundberg

2020

Catalysts

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The renewed interest in electrosynthesis demonstrated by organic chemists in the last years has allowed for rapid development of new methodologies. In this review, advances in enantioselective electrosynthesis that rely on catalytic amounts of organic or metal-based chiral mediators are highlighted with focus on the most recent developments up to July 2020. Examples of C-H functionalization, alkene functionalization, carboxylation and cross-electrophile couplings are discussed, along with their related mechanistic aspects.

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“…In 1992, Amundson and Balko reported an electrochemical Sharpless asymmetric dihydroxylation of 16 a with an Os‐ 16 c complex (Scheme ) . In this work, the traditional chemical oxidant was replaced by an anode to regenerate [Fe(CN) 6 ] 3− for the cycling of Os VIII from Os VI .…”

Section: Chiral Catalystmentioning

confidence: 99%

“…In 1992, Amundson and Balko reported an electrochemical Sharpless asymmetric dihydroxylation of 16 a with an Os-16 c complex( Scheme 16). [35] In this work, the traditional chemical oxidant was replaced by an anode to regenerate [Fe(CN) 6 ] 3À for the cyclingo fO s VIII from Os VI .L ater,T orii et al reported a similar system for dihydroxylation, [36] and the system wasd evelopedw ith iodine as mediator instead. [37] In 2015, Moeller and co-workers designedaphotovoltaic apparatus for electrochemicals ynthesis ande xamined its application in as imilar dihydroxylation reaction.…”

Section: Metal Catalysismentioning

confidence: 99%

Asymmetric Electrochemical Catalysis

Lin

Luo

2019

Chemistry A European J

139

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Asymmetric electrochemical catalysis, an emerging frontline in asymmetric catalysis and electro‐organic synthesis, is summarized. Representative works are classified, with respect to the external chiral resources, including chiral media, chiral mediator, chiral catalyst, and chiral electrode. This concept article is expected to provide readers with the general concepts and perspectives of each chiral electrochemical catalysis mode, and to indicate the potential and future development of asymmetric electrochemical catalysis.

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Preparation of chiral diols by the osmium-catalysed, indirect anodic oxidation of olefins

Cited by 33 publications

References 10 publications

Basic Strategies and Types of Applications in Organic Electrochemistry

Basic Strategies and Types of Applications in Organic Electrochemistry

Recent Advances in Asymmetric Catalytic Electrosynthesis

Asymmetric Electrochemical Catalysis

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