Synthesis of β-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol Ether by Visible Light Photoredox Catalysis

2022 ◽  
Author(s):  
Haoying Cao ◽  
Shanshan Ma ◽  
Yanhong Feng ◽  
Yawen Guo ◽  
Peng Jiao
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ether ◽  
Tertiary Carbon

Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones under visible light photoredox catalysis, which...

Carbon-carbon bond formation in reactions of PhIO.cntdot.HBF4-silyl enol ether adduct with alkenes or silyl enol ethers

1989 ◽  
Vol 54 (11) ◽  
pp. 2605-2608 ◽  
Author(s):  
V. V. Zhdankin ◽  
M. Mullikin ◽  
Rik Tykwinski ◽  
Bruce Berglund ◽  
Ronald Caple ◽  
...  
Keyword(s):  
Bond Formation ◽  
Enol Ether ◽  
Enol Ethers ◽  
Carbon Bond ◽  
Silyl Enol Ethers ◽  
Carbon Carbon Bond ◽  
Silyl Enol Ether

An Access to Highly Enantioenriched cis-3,5-Disubstituted γ-Lactones from α-Bromoacetate and Silyl Enol Ether

2021 ◽  
Author(s):  
Ha Rim Lee ◽  
Seo Yun Kim ◽  
Min Ji Park ◽  
Yong Sun Park
Keyword(s):  
Nucleophilic Substitution ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Synthetic Strategy ◽  
Silyl Enol Ether

A novel synthetic strategy for highly enantioenriched cis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of...

ChemInform Abstract: Carbon-Carbon Bond Formation in Reactions of PhIO·HBF4/Silyl Enol Ether Adduct with Alkenes or Silyl Enol Ethers.

ChemInform ◽  
1989 ◽  
Vol 20 (47) ◽  
Author(s):  
V. V. ZHDANKIN ◽  
M. MULLIKIN ◽  
R. TYKWINSKI ◽  
B. BERGLUND ◽  
R. CAPLE ◽  
...  
Keyword(s):  
Bond Formation ◽  
Enol Ether ◽  
Enol Ethers ◽  
Carbon Bond ◽  
Silyl Enol Ethers ◽  
Carbon Carbon Bond ◽  
Silyl Enol Ether

scholarly journals Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether

RSC Advances ◽  
2020 ◽  
Vol 10 (46) ◽  
pp. 27874-27883
Author(s):  
Makoto Shimizu ◽  
Shingo Hata ◽  
Koichi Kondo ◽  
Kazuhiro Murakami ◽  
Isao Mizota ◽  
...  
Keyword(s):  
Addition Reactions ◽  
Amino Ketone ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Iminium Salts ◽  
Silyl Enol Ether ◽  
Silyl Acetals

While iminium salts generated from amino ketene silyl acetals react with silyl enol ethers, those from amino silyl enol ethers also undergo facile addition reactions to give alpha-amino ketone derivatives in good yields.

Visible light-induced palladium-catalyzed ring opening β-H elimination and addition of cyclobutanone oxime esters

2019 ◽  
Vol 55 (95) ◽  
pp. 14291-14294 ◽  
Author(s):  
Wei-Long Xing ◽  
Rui Shang ◽  
Guang-Zu Wang ◽  
Yao Fu
Keyword(s):  
Visible Light ◽  
Ring Opening ◽  
Enol Ether ◽  
Radical Ring ◽  
Silyl Enol Ether ◽  
Palladium Catalyzed

A photo-excited Pd(0) complex activates cyclobutanone oxime esters to induce radical ring opening for the generation of products of β-H elimination and addition with silyl enol ether.

Synthesis of Mannich bases from electrochemically generated iminium salts in the presence of silyl enol ethers

1983 ◽  
Vol 61 (7) ◽  
pp. 1379-1382 ◽  
Author(s):  
Roger N. Renaud ◽  
Denis Bérubé ◽  
Campbell J. Stephens
Keyword(s):  
Tertiary Amine ◽  
Mannich Bases ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Iminium Salts ◽  
Iminium Salt ◽  
Factors Influencing ◽  
Silyl Enol Ether ◽  
Operating Potential

The formation of Mannich bases from the reaction of silyl enol ethers with N-methyl-N-mesitylmethyleniminium salt, generated by the electrochemical oxidation of N,N-dimethylmesidine, was studied. Important factors influencing the reaction are: (a) the silyl enol ether must be nucleophilic enough to react with the iminium salt and, at the same time, must be more difficult to oxidize than the tertiary amine, (b) the product of the reaction must not be oxidized at the operating potential. Examples are presented in this paper illustrating the successes and limitations of this reaction.

Photocatalytic Decarboxylative Alkylation of Silyl Enol Ether and Enamide with N-(Acyloxy)phthalimide using Ammonium Iodide

2021 ◽  
Author(s):  
Can Liu ◽  
Ni Shen ◽  
Rui Shang
Keyword(s):  
Catalytic Amount ◽  
Ammonium Iodide ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Silyl Enol Ether ◽  
Tetrabutylammonium Iodide

Enamides and silyl enol ethers were alkylated to deliver products of N-acyl imines and ketones in the presence of a catalytic amount of N-tetrabutylammonium iodide under irradiation of purple light...

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