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This report presents an overview of the synthesis and use of halovinyl (chloro- and bromovinyl) aldehydes as synthetic tools in organic chemistry. The present review focuses on the chemistry of halovinyl aldehydes in the last 18 years from 1989 to mid-2007, because these compounds are still of...
Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH 4 in DME or lithium tri- tert -butoxyaluminum hydride (LTBA) in THF at −60 °C. The former is a new approach that offers slightly greater diastereoselectivity in the reduction of...
We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends on the dienes...
The chemo- as well as regioselective imino Diels–Alder reactions of 5-dienyl pyrimidinones with N -aryl as well as N -naphthyl imines in the presence of a different Lewis acid catalysts resulting in novel quinoline and benzoquinoline derivatives are reported.
Reactions of 3-(polyfluoroacyl)chromones with acetoacetamide and ethyl acetoacetate in the presence of ammonium acetate proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent cyclization to 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinamides, ethyl...
Three-component coupling of carbonyl compounds, homoallylic alcohols, and nitriles has been achieved using 20 mol % of phosphomolybdic acid (PMA) at ambient temperature via the Prins–Ritter sequence to furnish 4-amidotetrahydropyrans in high yields with all cis selectivity....
The preparations are described of 35 new bridging ligands from five bisphenols through coupling each with seven different heterocyclic units. X-ray crystal structures of five representative examples revealed different conformations in the solid state with the terminal nitrogen donors being...
Fluorescent conjugates of N -benzyloxycarbonyl protected γ-aminobutyric acid were prepared by coupling to its C- terminus several polyheteroaromatic, based on the oxobenzopyran skeleton (trivially known as coumarin) and polyaromatic labels, such as naphthalene and pyrene. Photophysical...
Enantioselective synthesis of γ-aryl-γ-butyrolactones is achieved using ( S )-1-phenylethylamine as a chiral auxiliary. The synthesis involves cascade formation–destruction–formation of the chiral centre with a delayed stereoselective step. The actual stereoselective step has been found to...
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