Convergent paired electrolysis for zinc-mediated diastereoselective cinnamylation of α-amino esters

Park, Hahyoun; Kim, Minjun; Kang, Jungtaek; Song, Hyunjoon; Kim, Hyunwoo

doi:10.1039/d3cc01197f

“…Mei reported a TEMPO‐mediated enantioselective oxidative C−C coupling of N ‐aryl glycinates with ketones through electrolysis that proceeds via the formation of an imine intermediate [12] . Very recently, Kim unveiled zinc‐mediated electrochemical diastereoselective cinnamylation of α ‐amino esters with the help of convergent paired electrolysis [13] . Based on our expertise in electrosynthesis, [14] herein we report a mediator‐free electrochemical [3+2] cycloaddition strategy between α ‐amino carbonyls and tosylmethyl isocyanide to fabricate 1,5 substituted imidazoles devoid of any metal catalyst or external redox reagent (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Electrochemical [3+2] Cycloaddition between α‐Amino Carbonyls and Tosylmethyl Isocyanide en route to Substituted Imidazoles

Mallick,

Baidya,

De Sarkar

2023

Adv Synth Catal

9

0

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The established strategy unveils a metal and mediator‐free electrochemical [3+2] cycloaddition approach among α‐amino carbonyls and tosylmethyl isocyanide (TosMIC) fabricating substituted imidazole scaffolds. Implementation of electro‐redox conditions on this cycloaddition approach eliminates the essential requirement of transition metal catalysts and chemical oxidants. A wide variety of different functionalities are well tolerated under this reaction condition, contributing to the substrate scope and applicability. Several control experiments and cyclic voltammetry studies suggest an electro‐oxidation triggered successive C−C and C−N bond formations followed by rapid aromatization for constructing the five‐membered core structure.

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Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes

Yang,

Feng,

Qiu

2023

Angewandte Chemie

2

0

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Despite widespread use of the deuterium isotope effect, selective deuterium labeling of chemical molecules remains a major challenge. Herein, a facile and general electrochemically driven, organic mediator enabled deuteration of styrenes with deuterium oxide (D2O) as the economical deuterium source was reported. Importantly, this transformation could be suitable for various electron rich styrenes mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition‐metal catalysts, affording the desired products in good yields with excellent D‐incorporation (D‐inc, up to >99 %). Mechanistic investigations by means of isotope labeling experiments and cyclic voltammetry tests provided sufficient support for this transformation. Notably, this method proved to be a powerful tool for late‐stage deuteration of biorelevant compounds.

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Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes

Yang,

Feng,

Qiu

2023

View full text Add to dashboard Cite

Despite widespread use of the deuterium isotope effect, selective deuterium labeling of chemical molecules remains a major challenge. Herein, a facile and general electrochemically driven, organic mediator enabled deuteration of styrenes with deuterium oxide (D2O) as the economical deuterium source was reported. Importantly, this transformation could be suitable for various electron rich styrenes mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition‐metal catalysts, affording the desired products in good yields with excellent D‐incorporation (D‐inc, up to >99 %). Mechanistic investigations by means of isotope labeling experiments and cyclic voltammetry tests provided sufficient support for this transformation. Notably, this method proved to be a powerful tool for late‐stage deuteration of biorelevant compounds.

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Convergent paired electrolysis for zinc-mediated diastereoselective cinnamylation of α-amino esters

Abstract: A paired electrochemical method is presented for the one-pot synthesis of γ,δ-unsaturated α-amino esters.

Cited by 7 publications

References 37 publications

Metal‐Free Electrochemical [3+2] Cycloaddition between α‐Amino Carbonyls and Tosylmethyl Isocyanide en route to Substituted Imidazoles

Metal‐Free Electrochemical [3+2] Cycloaddition between α‐Amino Carbonyls and Tosylmethyl Isocyanide en route to Substituted Imidazoles

Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes

Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes

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