One-pot synthesis of tropinone by tandem (domino) ene-type reactions of acetone silyl enol ethers.
نویسندگان
چکیده
A synthetic approach for tropane alkaloids on the basis of tandem (domino) ene-type reactions of acetone silyl enol ethers with iminium ions is shown to be triggered by intermolecular ene-type reactions followed by 6-(2,5) silatropic ene-type cyclizations.
منابع مشابه
Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines.
A variety of functionalized 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes were prepared by one-pot cyclizations of 1,3-bis(silyl enol ethers) with quinazolines. The mechanism of the cyclization was studied by B3LYP/6-31G(d) density functional theory computations. The products could be functionalized by Suzuki cross-coupling reactions. The reaction of 1,3-bis(silyl enol ethers) with phth...
متن کاملSynthesis and characterization of novel silyl derivatives of curcumin
Abstract:Turmeric is a member of the ginger family (Zingiberaceae), which is extensively used as a spice, food preservative and colouring material. Curcumin is a main bioactive natural compound derived from the rhizome of this plant. Curcumin can exist in several tautomeric forms, keto and enol. The keto form is more stable than enol form. Silyl ethers have proven to be versatile substrates for...
متن کاملFacile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition
A triflic imide (Tf(2)NH) catalyzed isomerization of kinetically favourable silyl enol ethers into thermodynamically stable ones was developed. We also demonstrated a one-pot catalytic reaction consisting of (2 + 2) cycloaddition and isomerization. In the reaction sequence, Tf(2)NH catalyzes both of the reactions.
متن کاملFormal (3+3) cycloaddition of silyl enol ethers catalyzed by trifric imide: domino Michael addition-claisen condensation accompanied with isomerization of silyl enol ethers.
We describe here a Tf₂NH-catalyzed formal (3+3) cycloaddition of silyl enol ethers with acrylates as a new domino reaction. In the domino sequence, the catalyst activates Michael addition, deprotonation of the resulting silyloxonium cation and intramolecular Claisen condensation. It was found that reaction modes significantly depend on the reaction temperature. We also examined the mechanistic ...
متن کاملIn situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers.
Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes(2)Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 22 شماره
صفحات -
تاریخ انتشار 2002