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A three-step methodology involving an external chiral ligand-mediated asymmetric addition of phenyllithium to an anisidine imine, oxidative removal of N -PMP group, and finally oxidative conversion of the phenyl group to a carboxyl group provides a facile synthesis of optically pure α-amino acid...
The unsymmetrical mesoionic münchnones 13 (3-benzyl-2-methyl-4-phenyl-1,3-oxazolium-5-olate) and 14 (3-benzyl-4-methyl-2-phenyl-1,3-oxazolium-5-olate) react with the N -protected 2- and 3-nitroindoles 1 (ethyl 2-nitroindole-1-carboxylate), 6 (3-nitro-1-(phenylsulfonyl)indole), and 17 (ethyl...
An asymmetric desymmetrization of saturated and unsaturated cyclic and acyclic meso -1,2-diols has been developed from the ene acetals, prepared from the norbornene carboxyaldehyde and meso -1,2-diols. The intramolecular haloetherification of the ene acetals as a key step afforded 8-membered...
5-(Trifluoromethanesulfonyloxy)-4 H -1,3-dioxin ( 3 ) participates in a variety of nucleophilic substitution reactions with cuprate reagents or in palladium catalyzed cross-coupling reactions to provide 5-substituted-4 H -1,3-dioxins 5 . Upon thermolysis, these compounds undergo facile...
A series of amidosulfoxides were prepared by the addition of thiophenol to the appropriate alkenoic acid π-bond, and this was followed by reaction of the in situ generated acyl chloride with 3,4-dimethoxyphenethyl amine. The silicon-induced Pummerer reaction of these amidosulfoxides was carried...
Bis(alkylthio)carbenes have been shown to be a useful class of reactive intermediates for applications to organic synthesis. Substituted hydroindolones, isatins and hydroquinolones can be prepared by the addition of these carbenes to vinyl isocyanates.
Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione ( 16 ). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common...
Ceric ammonium nitrate oxidizes unsaturated ketene dithioacetals in wet MeCN to give cation radicals that cyclize to trisubstituted double bonds and styrenes by cation-like cyclizations leading to cyclic cation radicals that are transformed by further oxidation, hydrolysis and cyclization to...
Cyclization of tri- and tetrasubstituted dienones 1 under Lewis acidic conditions in the presence of triethylsilane led to formation of either silyl enol ethers 6 or cyclopentanones 7 in good to excellent yields, depending on work-up conditions. The proposed mechanism involves initial Nazarov...
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