Stereochemical studies of the electrolytic reactions of organic compounds. 19. Electroorganic reactions on organic electrodes. 1. Asymmetric reduction of prochiral activated olefins on a poly-L-valine-coated graphite

Abe, Shigemitsu; Nonaka, Tsutomu; Fuchigami, Toshio

doi:10.1021/ja00349a046

Cited by 58 publications

(15 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We also have an interest in exploring the electrochemistry of chiral surfaces (7,8). For these reasons the synthesis of l c , which contains both a chiral center and planar chirality, and its binding to silica, was an attractive target since, if necessary, it could readily be prepared as an optically pure enantiomer (9,10).…”

mentioning

confidence: 99%

The synthesis and structure of

Butler¹,

Cullen²,

Rettig³

1987

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

The synthesis and structure of

Butler¹,

Cullen²,

Rettig³

1987

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…In 1983, Nonaka et al explored the applicability of a poly-ʟ-valine 6 coated graphite cathode for asymmetric electrochemical reductions in two consecutive reports. In the first communication, they carried out the asymmetric reduction of prochiral activated olefins 5 and 8 , affording 7 and 9 with optical yields of 25% and 43%, respectively (Scheme 3) [23]. In the second report, the same electrode was applied for the asymmetric reduction of prochiral carbonyl compounds 10a and 12a , oximes 14 and gem -dibromo compounds 16 (Scheme 4).…”

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.

164

105

View full text Add to dashboard Cite

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.

show abstract

“…Osa and co‐workers reported an electrochemical asymmetric reduction of 2‐hexanone to 2‐hexanol by using Raney nickel electrodes modified with optically active tartaric acid . Later, the Nonaka group found that a poly‐( l ‐valine)‐coated graphite electrode was effective for the reductive transformation of prochiral olefins and oximes . The results of these attempts in enantioselective recognition and asymmetric synthesis on modified chiral electrodes, however, were not very satisfying.…”

Section: Chemically Modified Chiral Electrodesmentioning

confidence: 99%

Asymmetric Electrochemical Transformations

Chang

Guo

2020

Angewandte Chemie

View full text Add to dashboard Cite

The field of electrochemical synthesis has developed rapidly over the last decade and has provided alternative synthetic methods with the absence of stoichiometric amounts of chemical oxidants or reductants. Although sustainable electrosynthetic procedures have been developed, relatively few examples of highly enantioselective catalytic electrosynthesis have been reported to date. The development of general strategies for electrochemical enantiocontrol has thus proven to be a considerable challenge. This Minireview highlights the current knowledge and recent advances in the synthetic utility of electrochemical transformations for asymmetric synthesis. Specifically, three major types of catalytic enantioselective strategy in electrosynthesis are outlined, including electrochemical activation of chiral catalyst‐bound substrates, asymmetric cascade electrochemical processes, and chemically modified chiral electrodes.

show abstract

Stereochemical studies of the electrolytic reactions of organic compounds. 19. Electroorganic reactions on organic electrodes. 1. Asymmetric reduction of prochiral activated olefins on a poly-L-valine-coated graphite

Cited by 58 publications

References 2 publications

The synthesis and structure of

The synthesis and structure of

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

Asymmetric Electrochemical Transformations

Contact Info

Product

Resources

About