Total synthesis of (±)-Englerin A has been achieved starting from γ,δ-ynone 5 in 14 steps. The key feature of this synthesis is the highly efficient and stereoselective preparation of 8-oxabicyclo[3.2.1]octane derivative 6, a core skeleton of Englerin A, based on an inverse electron-demand [3+2] cycloaddition reaction of the platinum-containing carbonyl ylide, which was developed in our laboratory.
Ruthenium-catalyzed ortho-selective acylation of arylpyridines with acyl chlorides via CH bond cleavage is described. Aromatic acyl chlorides as well as ¡,¢-unsaturated acyl chlorides were coupled with arylpyridines to give aromatic ketones in the presence of [RuCl 2 (PPh 3 ) 3 ] as a catalyst and potassium carbonate as a base.Direct functionalization of arenes via regioselective CH bond cleavage by transition-metal catalysts has been one of the most extensively studied areas in organometallic catalysis in the past decade.
We report a borrowing hydrogen strategy for a palladium-catalyzed dehydrative coupling of aminoisoquinolines with benzylic alcohols in water. This cascade reaction using the π-benzylpalladium system can be achieved in an atom-economic process without the need for base or other additives, furnishing the N-benzylated aminoisoquinolines in moderate to excellent yields along with water as the sole co-product. The crossover experiment using [D 7 ]benzyl alcohol and 4-methoxybenzyl alcohol afforded H/D scrambled products. KIE experi- [a]
A facile synthetic procedure for the production of N-alkylated 3,4-dihydroisoquinolinone derivatives is described. The desired products were obtained by N-alkylation of 3,3 0 -dimethyl-3,4-dihydroisoquinoline derivatives followed by oxidation of the resulting iminium salts. Reaction conditions for both steps were very mild and the desired cyclization products could be obtained in good yield. This strategy allows the generation of N-substituted 3,4-dihydroisoquinolinone derivatives with substituents at the 3-position.
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