Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte

Maekawa, Hirofumi; Itoh, Kotaro; Goda, Satoshi; Nishiguchi, Ikuzo

doi:10.1002/chir.10165

Cited by 20 publications

(14 citation statements)

References 24 publications

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“…In 2003, Nishiguchi’s group explored the anodic oxidation of enol acetates 57 upon constant current electrolysis in an undivided cell at −78 ºC in a mixture of solvents containing ( S )-tetraethylammonium camphorsulfonate 58 as a chiral supporting electrolyte [58]. This resulted in the corresponding α-acetoxy ketones 59 , with low to moderate ee values (Scheme 23).…”

Section: Reviewmentioning

confidence: 99%

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

Ghosh

Shinde

Rueping

2019

Beilstein J. Org. Chem.

151

101

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The direct exploitation of ‘electrons’ as reagents in synthetic organic transformations is on the verge of a renaissance by virtue of its greenness, sustainability, atom economy, step economy and inherent safety. Achieving stereocontrol in such organic electrochemical reactions remains a major synthetic challenge and hence demands great expertise. This review provides a comprehensive discussion of the details of stereoselective organic electrochemical reactions along with the synthetic accomplishments achieved with these methods.

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Section: Reviewmentioning

confidence: 99%

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

Ghosh

Shinde

Rueping

2019

Beilstein J. Org. Chem.

151

101

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“…In 2003, Nishiguchi and co‐workers reported the enantioselective anodic oxidation of enol acetates utilizing 4 a as the supporting electrolyte (Scheme ) . Up to 37 % ee was achieved but with rather poor yield.…”

Section: Chiral Mediamentioning

confidence: 99%

Asymmetric Electrochemical Catalysis

Lin

Luo

2019

Chemistry A European J

126

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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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“…Although it is well established that am agnetic field cannot provide the chiral preference, [1] using amagnetic field in conjunction with photoinduced processes can initiate an enantioselective process,for example,magnetochiral anisotropy. [2,3] It has also been shown that ametal electrode which is either chiral, [4] or coated with chiral molecules [5][6][7] or achiral film, [8,9] can display enantiospecific interactions with ar edox couple in solution. This enantiospecificity is commonly explained by the threedimensional spatial arrangement of the chiral surface molecule(s) and the enantiomer in solution, the "lock and key" model.…”

Section: Introductionmentioning

confidence: 99%

The Electron Spin as a Chiral Reagent

et al. 2019

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We show that enantioselective reactions can be induced by the electron spin itself and that it is possible to replace ac onventional enantiopure chemical reagent by spinpolarized electrons that provide the chiral bias for enantioselective reactions.Three examples of enantioselective chemistry resulting from electron-spin polarization are presented. One demonstrates the enantioselective association of ac hiral molecule with an achiral self-assembled monolayer film that is spin-polarized, while the other two show that the chiral bias provided by the electron helicity can drive both reduction and oxidation in enantiospecific electrochemical reactions.Ineach case,the enantioselectivity does not result from enantiospecific interactions of the molecule with the ferromagnetic electrode but from the polarized spin that crosses the interface between the substrate and the molecule.F urthermore,t he direction of the electron-spin polarization defines the handedness of the enantioselectivity.T his work demonstrates an ew mechanism for realizing enantioselective chemistry.

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Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte

Cited by 20 publications

References 24 publications

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

Asymmetric Electrochemical Catalysis

The Electron Spin as a Chiral Reagent

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