Metal triflates-catalyzed conjugate addition of homochiral Pyrroles to alpha,beta-unsaturated esters

Unaleroglu, C
Temelli, B
Demir, Ayhan Sıtkı
The Friedel-Crafts reaction of homochiral pyrrole derivatives with alpha,beta-unsaturated esters catalyzed by metal triflates furnished conjugate addition products. The best yields were obtained by using yttrium triflate and methyl 4-phenyl-2-oxobut-3-enoate (2a). The addition worked regioselectively at C-5 of pyrrole. The diastereoisomers were separated by column chromatography.


Benzaldehyde Lyase-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
Ayhan, Peruze; Demir, Ayhan Sıtkı (Wiley, 2011-03-07)
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with nitroso compounds and furnishes N-arylhydroxamic acids in high yields. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to their reaction with nitroso compounds. The kinetic resolution of rac-2-hydroxy-1,2-diphenylethanones furnished (S)-benzoins and arylhydroxamic acids with high enantioselectivities and conversions.
Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates
Demir, Ayhan Sıtkı; Aybey, Asuman; Emrullahoglu, Mustafa (Georg Thieme Verlag KG, 2009-05-18)
Cyanide ion catalyzed addition of acylphosphonates to diethyl cyanophosphonate furnished phosphonocyanohydrin O-phosphates in high yield. The reaction works via the phosphonate-phosphate rearrangement, followed by the addition of diethyl cyanophosphonate to the cyanohydrin phosphate anion.
Manganese(iii)acetate-based free-radical additions of -dicarbonyl compounds to bicyclic systems
Fedalla, Mohammad Ali; Balcı, Metin; Department of Chemistry (2007)
Additions of carbon-centered radicals to alkenes are useful method for cyclic compounds formation. Manganese(III)-based oxidative free-radical cyclizations, where the radicals are generated and terminated oxidatively, are established as efficient methods for the construction of cyclic molecule. Treatment of a mixture of dimedone, Mn(OAc)3, and Cu(OAc)2 in glacial acetic acid with homobenzonorbornadiene (80) (4h at 50 C) gave furan derivative (107), dihydrofuran adduct (108), in addition to rearranged produc...
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives
Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
ROMP-polymers, in asymmetric catalysis: The role of the polymer backbone
Bolm, C; Tanyeli, Cihangir; Grenz, A; Dinter, CL (Wiley, 2002-08-01)
Ring-opening metathesis polymerization (ROMP) is utilized for the synthesis of highly functionalized polymers with covalently bound chiral prolinol units. The linear macromolecules act as multifunctional ligands in homogeneous asymmetric catalysis. The solubility of the polymers and their catalytic performance can be tuned by random copolymerization with achiral units in a simple and flexible manner. Use of norbornenes with additional well-defined stereogenic centers in the polymerizable core of the monomer...
Citation Formats
C. Unaleroglu, B. Temelli, and A. S. Demir, “Metal triflates-catalyzed conjugate addition of homochiral Pyrroles to alpha,beta-unsaturated esters,” SYNTHESIS-STUTTGART, pp. 2574–2578, 2004, Accessed: 00, 2020. [Online]. Available: