Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams

Aydogan, F
Demir, Ayhan Sıtkı
Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amino alcohols and 5-chloro-3-pentene-2-one. The photooxygenation of these compounds in the presence of a photosynthesizer furnishes the pyrrolooxazolone structures in high diastereoselectivities. In all of the examples, trans-isomers are formed as the major products.


Synthesis of n-(2-propylphenyl) substituted chiral amino alcohols and their usage in enantioselective diethylzinc addition reactions
Günler, Zeynep İnci; Tanyeli, Cihangir; Department of Chemistry (2011)
IChiral 1,2-amino alcohols were synthesized via newly developed “intramolecular unsaturation transfer” using cyclohexanone, propargyl bromide, and various chiral amino alcohols as starting components. These amino alcohols can be potential chiral ligands for many asymmetric transformation reactions. Therefore, their effectiveness as chiral ligands in diethylzinc addition to benzaldehyde and N-diphenylphosphinoyl imines were tested. Various parameters including temperature, solvent, ligand amount etc. were sc...
Synthesis of a novel poly(arylene ether ketone) and its conducting composites with polypyrrole
Selampinar, F; Akbulut, Ural; Yildiz, E; Gungor, A; Toppare, Levent Kamil (1997-08-01)
The synthesis of a 1,3-bis(4-fluorobenzoyl)-5-tert-butyl benzene and hexafluoro bisphenol A based poly(arylene ether ketone) (PEK) was described. The electrically conductive composites of polypyrrole (PPy) and PEK were formed by electropolymerization of pyrrole on a PEK coated platinum electrode in a medium containing water and p-toluenesulfonic acid as the solvent and the electrolyte, respectively. The electrical conductivity of the composites was found to be between 1 and 4 S/cm. The polypyrrole/poly( eth...
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...
Synthesis and characterization of conducting copolymers of menthyl ester of 3-thiophene acetic acid with pyrrole
Kiralp, S; Alkan, S; Toppare, Levent Kamil; Cianga, I; Yagci, Y (2003-01-01)
A new thiophene derivative containing menthyl group (MM) was synthesized and polymerized via chemical and electrochemical (constant current) methods. Polymers obtained and MM itself were used to synthesize copolymers with pyrrole under conditions of constant potential electrolyses. Cyclic voltammetry (CV), thermal analysis (DSC, TGA) and scanning electron microscopy (SEM) analyses were performed for the characterization of samples.
Synthesis and characterization of perylene tetracarboxylic propargyl esters as precursor materials for light-harvesting perylene derivatives in organic photonic applications
Sawalha, Mohamad; Özser, Mustafa Erkut; Sustainable Environment and Energy Systems (2021-9)
In this study, two isomerically pure perylene tetracarboxylic propargyl ester derivatives (P4 and P11) were synthesized and characterized to be used as intermediate compounds for bipolar perylene derivatives. The synthesized intermediates are extremely valuable and versatile building blocks, and their optical, photophysical, and electrochemical properties can be further tuned by the attachments of suitable electron-donating groups at the peri or bay positions. Electron-donor azidofluorene was combined with...
Citation Formats
F. Aydogan and A. S. Demir, “Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams,” TETRAHEDRON-ASYMMETRY, pp. 259–265, 2004, Accessed: 00, 2020. [Online]. Available: