THE NEW TYPE OF THE CHEMICAL CASCADE REACTION WAS FOUND formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48-93% yields. The latter are well-known prec...

Starting from unsaturated carbonyl compounds a mild new cascade reaction involving enolboration, rhodium-catalysed hydroformylation and intramolecular aldol addition in a regio- and diastereoselective fashion leads to cyclic compounds containing highly-functionalised quaternary carbon centres.

We report the arylation and heteroarylation of α,α-difluoro-α-(trimethylsilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)2Cy as ligand. A broad range of electronically varied aryl and heteroaryl bromides underwent this transformation to afford α-aryl-α,α-difluoroacetamides in high yields. Due to the electrophilic...

Cycloadditions are among the most trusted of chemical transformations available to the synthetic chemist. The predictability of the transition state based on steric and electronic considerations allows for the strategic construction of complex molecular assemblies. While the Diels–Alder reaction has received the most attention, 1,3-dipolar cycloadditions have also maintained a place of prominen...

A copper-catalyzed radical 1,2-aryl migration in α,α-diaryl allylic alcohols is developed, leading to β-silyl carbonyl compounds in moderate to good yields. The migration of aryls with lower aromaticity is favored. This procedure features the employment of silanes as commercially available materials.

A series of beta-(N-tosyl)amino diazo carbonyl compounds have been prepared by nucleophilic condensation of N-tosylimines with acyldiazomethanes. The diazo decomposition of these diazo carbonyl compounds under various catalytic conditions, including Rh(II) carboxylates, Cu(I) and Cu(II) complexes, PhCO(2)Ag/Et(3)N, TsOH, and SnCl(2).2H(2)O, has been investigated. It was found that, in most case...

The Wittig reaction rate can be dramatically enhanced by irradiation of the reaction mixture containing an aldehyde or ketone; methoxymethyl(triphenyl)phosphonium chloride, potassium t-butoxide, and t BuOH with a commercial microwave oven. Carbonyl compound are converted to Witting products within three min. in good yields.

The first iridium-catalyzed enantioselective allylic alkylation of an olefinic C(sp2)–H bond – that ?,?-unsaturated carbonyl compound, is developed in cooperation with Lewis base catalysis.

The alkynyl bond of the title compound, C(14)H(19)NO, has a length of 1.170 (5) Å. The amide function shows a trans conformation with respect to the carbonyl group characterized by the torsion angle O-C-N-H of -176 (2)°. There is an inter-molecular N-H⋯O hydrogen bond between the amide function and the carbonyl group. In addition, weak inter-molecular hydrogen bonds stabilize the crystal struct...

The direct aldol-type condensation of aldehydes with ethyl diazoacetate catalyzed by the chiral complex of BINOL derivatives-Zr(O(t)Bu)(4) gave beta-hydroxy alpha-diazo carbonyl compounds with moderate enantioselectivities (53-87% ee). [reaction: see text]