FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines

Beksultanova, Nurzhan
Gözükara, Zeynep
Araz, Mihrimah
Bulut, Merve
Polat-Çakır, Sıdıka
Doğan, Özdemir
New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl-substituted pyrrolidines by the 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides. 2-Thienyl, 2-furyl, 2-, 3-, and 4-pyridyl aldimines were prepared and used with N-methylmaleimide, dimethyl maleate, tert-butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl-substituted pyrrolidines. 1,3-DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single-crystal X-ray analysis.


Fam-Ti catalyzed enantioselective alkynylation of aldehydes
KOYUNCU, Hasan; Doğan, Özdemir (American Chemical Society (ACS), 2007-08-16)
Ferrocenyl-substituted aziridinylmethanol (Fam-1) has been used as a chiral catalyst with titanium for enantioselective alkynylation of aromatic, heteroaromatic, aliphatic, and alpha,beta-unsaturated aldehydes to give the corresponding propargylic alcohols in up to 96% yield and 96% ee. The ligand can be prepared easily and recycled.
Fam-zinc catalyzed asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides and
Koyuncu, Hasan; Doğan, Özdemir; Department of Chemistry (2007)
In the first part of this study, four new chiral ligands (FAM) were synthesized and used in catalytic amounts in asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides. This method leads to the synthesis of chiral pyrrolidines, which are found in the structure of many biologically active natural compounds and drugs. It was found that using 10 mol% of one of these chiral ligands with different dipolarophiles (dimethyl maleate, dimethyl fumarate, methyl acrylate, tert-butyl acrylate, and Nmethylm...
Electrochemical polymerization of 9-fluorenecarboxylic acid and its electrochromic device application
Bezgin, Buket; CİHANER, ATİLLA; Önal, Ahmet Muhtar (Elsevier BV, 2008-09-01)
Poly(9-fluorenecarboxylic acid) (PFCA) was synthesized by electrochemical oxidation of 9-fluorenecarboxylic acid (FCA) using a mixture of nitromethane and boron trifluoride diethyl etherate as the solvent and tetrabutylammonium tetrafluoroborate as the supporting electrolyte. An insoluble and conducting brownish-orange film was deposited on the electrode surface, both during repetitive cycling and constant potential electrolysis at 1.15 V. Characterization of the polymer film has been carried out using Four...
Particulate matter (PM10) in Istanbul: Origin, source areas and potential impact on surrounding regions
Koçak, Mustafa; Zarmpas, P.; Im, U.; Bougiatioti, A.; Yenigun, O.; Mihalopoulos, N. (2011-12-01)
Water-soluble ions (Cl-, NO3-, SO42-, C2O4-, Na+, NH4+, K+, Mg2+,Ca2+), water soluble organic carbon (WSOC), organic and elemental carbon (OC, EC) and trace metals (Al, Ca, Ti, V. Cr, Mn, Fe, Ni, Cu, Zn, Cd and Pb) were measured in aerosol PM10 samples above the megacity of Istanbul between November 2007 and June 2009. Source apportionment analysis using Positive Matrix Factorization (PMF) indicates that approximately 80% of the PM10 is anthropogenic in origin (secondary, refuse incineration, fuel oil and s...
Polystyrene-b-poly(2-vinyl phenacyl pyridinium) salts as photoinitiators for free radical and cationic polymerizations and their photoinduced molecular associations
Taskin, Omer Suat; Erel Göktepe, İrem; Khan, Muhammad Alyaan Ahmed; Pispas, Stergios; Yağcı, Yusuf (Elsevier BV, 2014-07-01)
Polystyrene-b-poly(2-vinyl phenacyl pyridinium hexafluorophosphate) (PS-b-PVPP) was synthesized by reacting polystyrene-b-poly(2-vinyl pyridine) prepared by living anionic polymerization with phenacyl bromide followed by counter anion exchange reaction. The ability of PS-b-PVPP to act as a photoinitiator for both free radical and cationic polymerizations is demonstrated. In the free radical polymerization, the initiation step involves the decay of the excited state of the salt with homolytic bond rupture of...
Citation Formats
N. Beksultanova et al., “FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines,” Chirality, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85106439011&origin=inward.