13735-81-4Relevant articles and documents
Triazene-Activated Donor-Acceptor Cyclopropanes: Ring-Opening and (3 + 2) Annulation Reactions
Dong, Zhaowen,Fadaei-Tirani, Farzaneh,Le Du, Eliott,Muriel, Bastian,Scopelliti, Rosario,Severin, Kay,Suleymanov, Abdusalom A.,Waser, Jér?me
, (2020)
Donor-acceptor cyclopropanes substituted with 3,3-dialkyltriazenyl groups are described herein. The strong electron-donating character of the triazene renders the cyclopropanes highly reactive, allowing for catalyst-free ring-opening reactions with methanol and tetracyanoethylene under mild conditions. The triazene-substituted cyclopropanes could also be used as substrates in Lewis acid catalyzed (3 + 2) annulations with silyl enol ethers.
A Convenient Regioselective Synthesis of Mannich Bases
Rochin, C.,Babot, O.,Dunogues, J.,Duboudin, F.
, p. 667 - 668 (1986)
A new, convenient regioselective process for aminomethylation of ketones is reported, involving the in situ formation of silyl enol ethers and iminium salts.
THE REACTION OF CHROMYL CHLORIDE AND O-SILYLATED ENOLATES: A NOVEL REGIOSPECIFIC ROUTE TO α-HYDROXY KETONES.
Lee, Thomas V.,Toczek, Judy
, p. 2917 - 2920 (1982)
Chromyl chloride reacts regiospecifically with O-silylated enolates to form α-hydroxy ketones.
A practical method for the preparation of trimethylsilyl enol ethers
Lin, Ji-Mao,Liu, Ben-Sheng
, p. 739 - 749 (1997)
In the mixed system of chlorotrimethylsilane/triethyl amine/N,N-dimethylformamide/potassium iodide/petroleum ether, aldehydes or ketones are silylated to silyl enol ethers at room temperature. The N,N-dimethylformamide/potassium iodide layer can be used as circulating liquor for many times. The yields are high.
Enantioselective Mukaiyama–Michael Reaction Catalyzed by a Chiral Rhodium Complex Based on Pinene-Modified Pyridine Ligands
Gong, Jun,Wan, Qian,Kang, Qiang
, p. 2484 - 2488 (2018)
The rhodium complex Λ-Rh1 containing chiral pinene-modified pyridine ligands is prepared through a two-step synthetic procedure; it exhibits excellent reactivity and enantiocontrol towards the enantioselective Mukaiyama–Michael reaction of α,β-unsaturated 2-acyl imidazoles with silyl enol ethers, affording enantioenriched 1,5-dicarbonyl compounds in good yields (up to 99 %) with excellent enantioselectivities (up to 99 % ee).
Use of 1,8-Diazabicycloundec-7-ene in Preparation of Trimethylsilyl Enol Ethers and Trimethylsilylacetylenes
Taniguchi, Yoshiyuki,Inanaga, Junji,Yamaguchi, Masaru
, p. 3229 - 3230 (1981)
Trimethylsilyl enol ethers were prepared by using a combination of chlorotrimethylsilane and 1,8-diazabicycloundec-7-ene in good yields.Trimethylsilylation of acetylenes was also achieved with the same reagents in the presence of silver salt as catalyst.
C?O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non-Rubottom Oxidation
Vil', Vera A.,Gorlov, Evgenii S.,Bityukov, Oleg V.,Barsegyan, Yana A.,Romanova, Yulia E.,Merkulova, Valentina M.,Terent'ev, Alexander O.
, p. 3173 - 3181 (2019)
Malonyl peroxides act both as oxidants and reagents for C?O coupling in reactions with methyl and silyl enol ethers. In the proposed conditions, the oxidative C?O coupling of malonyl peroxides with enol ethers selectively proceeds, bypassing the traditional Rubottom hydroxylation of enol ethers by peroxides. It was observed that the oxidative [5+2] cycloaddition of malonyl peroxides and enol ethers is the key stage of the discovered process. Oxidative C?O coupling of silyl enol ethers leads to the formation of α-acyloxyketones with a free carboxylic acid group. A specially developed preparative one-pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α-acyloxyketones with yields 35–88%. The acid-catalyzed coupling with methyl enol ethers gives remarkable products while retaining the easily oxidizable enol fragment. Furthermore, these molecules contain a free carboxylic acid group, thus these nontrivial products contain two usually incompatible acid and enol ether groups. (Figure presented.).
Changing course with an additive: A striking example of the effect of TMSCl on lithium amide reactivity
Harrowven, David C.,Poon, Hon Suen
, p. 4281 - 4282 (1996)
When a solution of diethyl maleate and acetophenone is added to a cooled (-78°C) solution of a lithium amide the maleate derivative 3 is given in good yield. Pre-treatment of the lithium amide with TMSCl alters the course of this reaction dramatically. With half an equivalent of this additive the Michael adduct 4 is given in 62% yield while employing three equivalents leads to the silyl enol ether 5 in >85% yield.
Palladium Catalyzed Reaction of Trimethylsilyltributyltin with α-Halo Ketones. Preparation of Enol Silyl Ethers
Kosugi, Masanori,Ohya, Takao,Migita, Toshihiko
, p. 3539 - 3540 (1983)
The reaction of trimethylsilyltributyltin with α-halo ketone in the presence of a catalytic amount of palladium chloride plus twice molar amounts of trimethyl phosphite gave enol silyl ethers in good yields.
Addition reaction of imidazoles and thiazoles with silyl enol ethers in the presence of alkyl chloroformate
Itoh, Takashi,Miyazaki, Michiko,Nagata, Kazuhiro,Ohsawa, Akio
, p. 4383 - 4395 (2000)
Silyl enol ethers and ketene silyl acetals reacted with imidazole, thiazole, and their benzo derivatives in the presence of an alkyl chloroformate to give 2-substituted imidazolines and thiazolines in good yields via the intermediacy of unstable N-acylated quaternary salts of azoles. In addition, it was found that silyl enol ethers formed in situ were also useful for the reaction to afford the adducts only by simple sequential addition of five commercially available reagents. (C) 2000 Elsevier Science Ltd.
