Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

Nokami, Toshiki; Shibuya, Akito; Saigusa, Yoshihiro; Manabe, Shino; Ito, Yukishige; Yoshida, Jun

doi:10.3762/bjoc.8.52

Cited by 32 publications

(10 citation statements)

References 30 publications

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“…Thus, we expected that electrochemical activation of thioglycoside 9 in the presence of tetrabutylammonium triflate (Bu 4 NOTf) might be a useful method to generate and accumulate glycosyl triflates 10 (Figure 3). [11–14] Indeed, a variety of glycosyl triflates 10 a – g have been generated electrochemically and utilized for glycosylation of alcohols, including hydroxyl groups of carbohydrates. Based on these results, we developed an automated electrochemical assembly as a methodology for the synthesis of oligosaccharides, as shown in Section 4.…”

Section: Electrochemical Generation Of Reactive Speciesmentioning

confidence: 99%

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Shibuya

Nokami

2021

The Chemical Record

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Electrochemical methods offer a powerful, reliable, and environmentally benign approach for the synthesis of small organic molecules, and such methods are useful not only for the transformation of small molecules, but also for the preparation of oligomers and polymers. Electrochemical assembly is a concept that allows structurally well‐defined middle‐sized organic molecules to be synthesized by applying electrochemical methods. The preparation of dendrimers, dendronized polymers, and oligosaccharides are introduced as examples of such an approach. Automated electrochemical assembly of oligosaccharides is also demonstrated using the electrochemical synthesizer developed by our group.

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Section: Electrochemical Generation Of Reactive Speciesmentioning

confidence: 99%

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Shibuya

Nokami

2021

The Chemical Record

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“…[ 3 ] It is unquestionable that transition‐metal‐catalyzed intramolecular C—H amination of 2‐amidobiaryls is a high performance strategy for the synthesis of carbazoles. [ 4‐5 ] Since the pioneering work in this area contributed by Buchwald and coworkers in 2005 using Pd(OAc) 2 as catalyst in the presence of Cu(OAc) 2 and dioxygen, this protocol has been developed extensively. [ 4a ] Later, it was found that Cu(OAc) 2 could be replaced by DMSO as the co‐oxidant by the same group.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Electrochemical Palladium‐Catalyzed Intramolecular C—H Amination of 2‐Amidobiaryls for Synthesis of Carbazoles

et al. 2020

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Electrosynthesis | Palladium-catalyzed | Cross coupling | Amination | Carbazoles The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C-H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.

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“…Electrochemical oxidation at low temperature is useful to generate and accumulate glycosyl triflates that are reactive but detectable by NMR ( Figure 11). [18][19][20][21] Although 4,6-benzylidene protection of mannoside is labile under anodicoxidation, introductiono fachlorine atom at the para-position of phenyl group is effective to stabilize the 4,6-benzylidene protection. Thus-prepared mannoside buildingb lock 16 d was used as a precursor of glycosyl triflate intermediate 38,w hich has a-stereochemistry as confirmed by 1 Ha nd 13 CNMR spectroscopy at low temperature.…”

Section: Direct Oxidation Of Thioglycosidesint He Absence Of Glycosylmentioning

confidence: 99%

Electrochemical Methods as Enabling Tools for Glycosylation

et al. 2018

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Electrochemical methods have been widelyu sed for organic synthesis including glycosylation. Electrochemical oxidation via single electron transfer (SET) is ap owerful method to activate varioust ypes of glycosyl donors. Their oxidation potentials, which reflect the reactivity of glycosyl donors under anodic oxidation conditions are tunable by changing protecting groups and the anomeric leaving groups of glycosyl donors. Not only thioglycosides but also other chalcogenoglycosides have been studied as highly reactive glycosyld onors.R ecently,a utomated electrochemical assembly,w hich is an automated electrochemical solutionphase synthesis of oligosaccharides was successfully demonstrated by the rational optimization of thioglycosides as both glycosyl donors and acceptors through electrochemical measurements and DFT calculations.[a] S. Manmode, Prof. T. Nokami, Prof. T. Itoh

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Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

Cited by 32 publications

References 30 publications

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Electrochemical Palladium‐Catalyzed Intramolecular C—H Amination of 2‐Amidobiaryls for Synthesis of Carbazoles

Electrochemical Methods as Enabling Tools for Glycosylation

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