Catalytic asymmetric one-pot synthesis of pyrrolidines via 1,3-dipolar cycloaddition reaction of azomethine ylides

Download

index.pdf

Date

2013

Author

Ayan, Seylan

Metadata

Show full item record

Item Usage Stats

60
views

28
downloads

In recent years one-pot reactions have been studied significiantly by different research groups. These reactions provide complex molecules from very simple starting materials in a single step. For that reason it is considered as atom economical reaction and “green chemistry”. Asymmetric versions of these reactions are also being studied by organic groups for the synthesis of complex chiral compounds. In this respect, we have studied metal catalyzed one-pot reaction of azomethine ylides with electron defficient dipolarophiles using chiral ligands with silver metal. As the chiral ligands amino alcohol based ferrocenyl aziridinyl methanol (FAM) and phosphorous based phosphino ferrocenyl aziridinyl methanol (PFAM) were used. These ligands have an advantage of being synthesized easily on a gram scale starting from acryloyl ferrocene. Moreover, the yellow color of ferrocene ease the purification by flash column chromatography. For the one-pot reaction glycine methyl ester, aromatic aldehyde, dipolarophile, chiral ligand, and silver salt were mixed in the same reaction flask to form pyrrolidine derivatives. Analysis of the reaction products showed that pyrrolidine derivatives can be obtained with up to 99% yield and 86% enantioselectivity by this catalytic asymmetric one-pot reaction.

Subject Keywords

Pyrrolizidines., Asymmetry (Chemistry)., Catalysis., Azomethine ylides.

URI

http://etd.lib.metu.edu.tr/upload/12616148/index.pdf
https://hdl.handle.net/11511/22764

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Kinetic studies for the production of tertiary ethers used as gasoline additives Boz, Nezahat; Doğu, Timur; Department of Chemical Engineering (2004) In the present study, the kinetics studies for etherification reactions were investigated in detail. In the first phase of present study, different acidic resin catalysts were prepared by the heat treatment of Amberlyst-15 catalysts at 220°C at different durations of time and also by the synthesis of sulfonated styrene divinylbenzene cross-linked resins at different conditions. A linear dependence of reaction rate on hydrogen ion-exchange capacity was in 2M2B+ethanol reaction. However, in the case of 2M1B+e...
Synthesis of 2-aziridinyl phosphonates by modified Gabriel-Cromwell reaction and their antibacterial activities Doğan, Özdemir; Gözen, Ayşe Gül (Elsevier BV, 2011-06-01) A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.
Enhancing electrochemical and electrochromic performances of carbazole comprising monomer via copolymerization with 3,4-ethylenedioxythiophene (EDOT) Kalay, Isil; Yigit, Deniz; GÜLLÜ, Mustafa; DEPCİ, TOLGA; Toppare, Levent Kamil; Hacioglu, Serife O. (Elsevier BV, 2020-09-01) In this study, two novel electrochromic copolymers (CoP1.3 and CoP1.5) were synthesized via electrochemical methods and characterized. The comonomers used in the synthesis were 3,4-ethylenedioxythiophene (EDOT) and a carbazole comprising monomer; 9-(2-(4-(Phenyldiazenyl) phenoxy) ethyl)-3,6-di(thiophen-2-yl)-9H-carbazole (M1). Carbazole containing monomer (M1) and EDOT were combined with two different comonomer feed ratios, 1: 3 and 1: 5 respectively in order to investigate the effect of increasing EDOT amo...
A new p-fam-silver catalyst for asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides Eröksüz, Serap; Doğan, Özdemir; Department of Chemistry (2008) In this study new twelve phosphorus based chiral ligands were synthesized and characterized. Then the catalytic activity of these chiral ligands was tested with Cu(II) and Ag(I) salts in asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides. This method provides the synthesis of different pyrrolidine derivatives with up to four stereogenic centers. Pyrrolidine derivatives are found in the structure of many biologically active natural compounds and drugs. Therefore the asymmetric synthesis of t...
Synthesis and Stimuli-Responsive Properties of Metallo-Supramolecular Phosphazene Polymers Based on Terpyridine Metal Complexes Sezer, Selda; KÖYTEPE, SÜLEYMAN; GÜLTEK, AHMET; SEÇKİN, TURGAY (2021-08-01) In this study, terpyridine functionalized phosphazene based metallo-supramolecular polymers were synthesized by three step reaction method. In the first step, 4 '-(4-aminophenyl)-2,2 ':6 ',2 ''-terpyridine was synthesized with p-nitro benzaldehyde and 2-acetylpyridine. Then, the monomer containing six terpyridine (TPY) units attached to the phosphazene was prepared from 4 '-(4-aminophenyl)-2,2 ':6 ',2 ''-terpyridine and hexachlorocyclotriphosphazene by a condensation reaction. Finally, metallo-supramolecula...

Citation Formats

S. Ayan, “Catalytic asymmetric one-pot synthesis of pyrrolidines via 1,3-dipolar cycloaddition reaction of azomethine ylides,” M.S. - Master of Science, Middle East Technical University, 2013.