Cerium(III) chloride-mediated vinylation of acylsilanes: A convenient new entry to silylated allylic alcohols
The reaction of alkyl, cycloalkyl, aromatic, heteroaromatic and α,β-unsaturated acylsilanes 1-7 and of homochiral acylsilanes 15 and 16 with the complex vinylmagnesium bromide/CeCl3 affords the silylated allylic alcohols in satisfactory to exce
BASE-INDUCED REARRANGEMENT OF 1-(TRIMETHYLSILYL)ALLYLIC ALCOHOLS. STEREO- AND REGIOSELECTIVE SYNTHESIS OF SILYL ENOL ETHERS THROUGH LITHIUM HOMOENOLATES.
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.
Kato,Mori,Oshino,Enda,Kobayashi,Kuwajima
p. 1773 - 1778
(2007/10/02)
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