76437-07-5Relevant academic research and scientific papers
Lithium hexamethyldisilazide-mediated enolizations: Influence of triethylamine on E/Z selectivities and enolate reactivities
Godenschwager, Peter F.,Collum, David B.
scheme or table, p. 8726 - 8732 (2009/02/02)
Lithium hexamethyldisilazide (LiHMDS) in triethylamine (Et 3N)/toluene is shown to enolize acyclic ketones and esters rapidly and with high E/Z selectivity. Mechanistic studies reveal a dimer-based mechanism consistent with previous studies of
REGIO- AND STEREODEFINED SYNTHESIS OF TRIMETHYLSILYL ENOL ETHERS RESULTED FROM THE ISOMERIZATION OF α-TRIMETHYLSILYL KETONES
Matsuda, Isamu,Sato, Susumu,Hattori, Motoaki,Izumi, Yusuke
, p. 3215 - 3218 (2007/10/02)
The isomerization of an α-trimethylsilyl ketone is lead to the corresponding trimethylsilyl enol ether with the enhanced regioselectivity by heating or by the assist of trimethylsilyl trifluoromethanesulfonate.The thermal reaction discloses a new regiodefined (E)-selective route to silyl enol ethers.
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.
