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...

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

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.

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...

scholarly journals Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

2011 ◽  
Vol 7 ◽  
pp. 648-652 ◽  
Author(s):  
Haruo Aikawa ◽  
Tetsuro Kaneko ◽  
Naoki Asao ◽  
Yoshinori Yamamoto
Keyword(s):  
Alkylating Agents ◽  
Gold Catalyst ◽  
Nucleophilic Attack ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Silyl Enol Ether ◽  
Leaving Groups ◽  
Acid Esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.

Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 665-673 ◽  
Author(s):  
Peter Langer ◽  
Zahid Hassan
Keyword(s):  
Cost Effective ◽  
Coupling Reactions ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Cross Coupling Reactions ◽  
Silyl Enol Ether ◽  
Synthetic Routes ◽  
Metal Catalyzed ◽  
High Level

This account describes our recent findings and progress in synthesizing chlorinated arenes and hetarenes by one-pot cyclizations of 1,3-bis-silyl enol ether derivatives. These reactions allow for the preparation of highly functionalized products with a high level of regioselectivity. The synthetic routes are cost-effective avoiding additional functionalization steps. The products are difficult to be accessed by other methods. The chlorine atom is of relevance in medicinal and agriculture chemistry. In addition, it allows further functionalizations by transition-metal-catalyzed cross-coupling reactions.1 Introduction2 Cyclizations of 2-Chloro-1,3-bis(silyloxy)-1,3-butadienes2.1 3,5-Dihydroxychlorophthalates2.2 2,4-Dihydroxy-homochlorophthalates2.3 2-(Arylsulfonyl)chloropyridines2.4 1-Azaxanthones3 Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes3.1 3-Chlorosalicylates3.2 Functionalized Chlorobiaryls3.3 3-Chloro-5-(2-chloroethyl)-salicylates3.4 2,4-Dihydroxychlorobenzophenones4 Cyclizations of 2-Chloro-3-(silyloxy)-2-en-1-ones4.1 Functionalized Chlorophenols4.2 Functionalized Chlorinated Biaryls and Chlorofluorenones4.3 Functionalized Chlorochromenones4.4 Functionalized 3-(Methylthio)chlorophenols4.5 Functionalized 3-Chloromethylphenols5 Conclusions6 List of Abbreviations

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