76437-02-0Relevant articles and documents
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.