The fragmentation reaction of differently functionalized [2.2.2]- and [2.2.1]bicyclic systems that leads to substituted five membered heterocycles and five/six membered carbocycles is broadly studied. This reaction is carried out through a retro-Dieckmann-type condensation on strained [2.2.1]bicyclic β-ketosulfones and their counterparts β-ketoesters under very mild catalytic acid or basic cond...

Some 2-hydroxy-4-methyl-6substituted quinoline derivatives have been synthesized in an environmentally benign method from easily available 4-substituted anilines and β-Ketoesters, under ordinary conditions. The reactions were catalyzed by aluminium chloride to afford excellent amount of the products. The usage of hazardous acids, bases and solvents have been avoided in different steps of the re...

A new organocatalytic asymmetric domino Michael-alkylation reaction of methyleneindolinones and γ-halogenated-β-ketoesters is described. A variety of spiro-cyclopentanoneoxindoles were obtained in high yields (up to 96%), good diastereoselectivities (up to 12 : 1 dr) and excellent enantioselectivities (up to >99% ee) via α-alkylation. Interestingly, O-alkylated products with tetronic acid motif...

We report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Brønsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli reaction conditions, the present method has the advantages of giving good yields, short reaction times, near room temperature conditions and the ...

The copper-catalyzed α-amination of carbonyl compounds using nitrosoformate intermediates as the electrophilic source of nitrogen is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. The scope of the reaction is broad in terms of both the N-substituted hydroxylamines and the β-ketoesters. The new methodology harnesses the power of nitrosoformate intermediates and demonst...

The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydr...

Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combin...

One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(III)/Co(II) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate a...