94287-27-1Relevant articles and documents
Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers
Schnell, Simon D.,Schilling, Mauro,Sklyaruk, Jan,Linden, Anthony,Luber, Sandra,Gademann, Karl
supporting information, p. 2426 - 2430 (2021/04/05)
The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.
Access to α-Pyrazole and α-Triazole Derivatives of Ketones from Oxidative Heteroarylation of Silyl Enolethers
Dhanju, Sandeep,Caravana, Aidan C.,Thomson, Regan J.
supporting information, p. 8055 - 8058 (2020/11/02)
The synthesis of α-pyrazole and α-triazole derivatives of ketones by the ceric ammonium nitrate-mediated oxidative coupling of enolsilanes with heteroarenes is reported. The reaction proceeds under mild reaction conditions to provide a diversity of products, including sterically hindered fully substituted derivatives.
Chiral Zinc(II)-Catalyzed Enantioselective Tandem α-Alkenyl Addition/Proton Shift Reaction of Silyl Enol Ethers with Ketimines
Kang, Tengfei,Cao, Weidi,Hou, Liuzhen,Tang, Qiong,Zou, Sijia,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 2464 - 2468 (2019/02/09)
A new catalytic asymmetric tandem α-alkenyl addition/proton shift reaction of silyl enol ethers with ketimines was serendipitously discovered in the presence of chiral N,N′-dioxide/ZnII complexes. The proton shift preferentially proceeded inste
Lewis acid-catalyzed nucleophilic substitutions of propargylic and allylic silyl ethers with enol silyl ethers
Ishikawa, Teruhiko,Aikawa, Toshiaki,Mori, Yumiko,Saito, Seiki
, p. 51 - 54 (2007/10/03)
(Matrix presented) Nucleophilic reactions of various enol silyl ethers with carbocation species generated from propargyl silyl ethers by the action of a Lewis acid have been developed. The present method is highly useful for the introduction of allenic or
Silazanes/catalytic bases: Mild, powerful and chemoselective agents for the preparation of enol silyl ethers from ketones and aldehydes
Tanabe, Yoo,Misaki, Tomonori,Kurihara, Minoru,Iida, Akira,Nishii, Yoshinori
, p. 1628 - 1629 (2007/10/03)
We have developed an efficient method for the preparation of enol silyl ethers using novel agents, silazanes together with NaH or DBU catalyst, wherein TMS and TBDMS groups were smoothly and chemoselectively introduced into ketones and aldehydes under mil
Direct transformation of silyl enol ethers into functionalized allenes
Langer, Peter,Doering, Manfred,Seyferth, Dietmar,Goerls, Helmar
, p. 573 - 584 (2007/10/03)
The first elimination reactions of silyl enol ethers to lithiated allenes are reported. These reactions allow a direct transformation of readily available silyl enol ethers into functionalized allenes. The action of three to four equivalents of lithium di
A stereoselective isomerization of allyl silyl ethers to (E)- Or (Z)-silyl enol ethers using cationic iridium complexes
Ohmura, Toshimichi,Shirai, Yasuo,Yamamoto, Yasunori,Miyaura, Norio
, p. 1337 - 1338 (2007/10/03)
A cationic indium complex, prepared via the hydrogenation of [Ir(cod)2]PF6-2PPr3 is found to be an excellent catalyst for the stereoselective isomerization of primary allyl silyl ethers to (E)-enol ethers and secondary all
RHODIUM(I)-CATALYZED ISOMERIZATION OF SILOXYCYCLOPROPANES LEADING TO ENOL SILYL ETHERS AND ALLYL SILYL ETHERS
Ikura, Kiyoshi,Ryu, Ilhyong,Ogawa, Akiya,Kambe, Nobuaki,Sonoda, Noboru
, p. 6887 - 6890 (2007/10/02)
The isomerization of siloxycyclopropanes to enol silyl ethers and allyl silyl ethers was accomplished by using 2 as a catalyst.Regiochemistry with respect to the newly formed double bond of the product was highly dependent on the substitution pattern of cyclopropane ring.