70424-35-0Relevant academic research and scientific papers
A FACILE SYNTHESIS OF α-TRIMETHYLSILYL KETONES AND THEIR REGIOSPECIFIC REARRANGEMENT TO TRIMETHYLSILY ENOL ETHERS
Sato, Susumu,Matsuda, Isamu,Izumi, Yusuke
, p. 3855 - 3858 (1983)
The rhodium catlyzed isomerization of β-trimethylsilylallyl alcohols has been successfully applied for the stepwise and selective synthesis of α-trimethylsilyl ketones and trimethylsilyl enol ethers.
Chemo- and regioselective preparation of zinc enolate from thiol esters by palladium catalyzed cross-coupling reaction
Haraguchi, Ryosuke,Ikeda, Zenichi,Ooguri, Akihiro,Matsubara, Seijiro
, p. 8830 - 8837 (2015/10/20)
The palladium catalyzed cross-coupling reaction of thiol esters with bis(iodozincio)methane or 1,1-bis(iodozincio)ethane gave Reformatsky-type enolates. They can react with some electrophiles to give the corresponding adducts and were also trapped by silylation reagents to afford silyl enol ethers. As the method applicable to the thiol ester carrying ketone moiety, it afforded zinc enolates carrying ketone in the same molecule.
BASE-INDUCED REARRANGEMENT OF 1-(TRIMETHYLSILYL)ALLYLIC ALCOHOLS. STEREO- AND REGIOSELECTIVE SYNTHESIS OF SILYL ENOL ETHERS THROUGH LITHIUM HOMOENOLATES.
Kato,Mori,Oshino,Enda,Kobayashi,Kuwajima
, p. 1773 - 1778 (2007/10/02)
1-(Trimethylsilyl)allylic alcohols have been prepared and their conversions to silyl enol ethers have been examined. Under appropriate conditions, lithium alkoxides of the above alcohols are in equilibrium with lithium homoenolates, 3-(trimethylsiloxy)allyllithiums, which react with alkyl iodides to give the silyl enol ethers of defined stereo- and regiochemistry. Further, a catalytic amount of butyllithium induces the rearrangement of the alcohols to yield the corresponding silyl enol ethers in a highly stereo- and regiocontrolled manner via self-protolysis. Equilibrium composition between lithium alkoxides and lithium homoenolates has been shown to be greatly influenced by the steric factors around alpha carbons of allylic alcohols.
STEREO- AND REGIO-SELECTIVE CONVERSION OF 1-TRIMETHYLSILYLALLYLIC ALCOHOLS INTO THE SILYL ENOL ETHERS CATALYZED BY BUTHYLLITHIUM
Kuwajima, Isao,Kato, Masahiro,Mori, Akio
, p. 2745 - 2748 (2007/10/02)
(Z)-Silyl enol ethers can be prepared selectively with complete regio-specificity by treating 1-trimethylsilylallylic alcohols with a catalytic amount of buthyllithium.
