ROMP-polymers, in asymmetric catalysis: The role of the polymer backbone

Bolm, C
Tanyeli, Cihangir
Grenz, A
Dinter, CL
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 monomers leads to polymers which show cooperative effects between the various elements of chirality during the course of the catalysis.


Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
Dengiz, Çağatay; GUTIERREZ, Gregory D.; SWAGER, Timothy M. (American Chemical Society (ACS), 2017-07-21)
The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels-Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF2, as observed by (HNMR)-H-1 analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels-Alder adduct 10 is additionally demonstrated and e...
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...
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: synthesis, in vitro evaluation, and molecular docking studies
Esiyok, Peruze Ayhan; Seven, Ozlem; Eymur, Guluzar; Tatar, Gamze Bora; DAYANGAÇ ERDEN, DİDEM; YELEKÇİ, Kemal; YURTER, HAYAT; Demir, Ayhan Sıtkı (The Scientific and Technological Research Council of Turkey, 2014-01-01)
New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl or morpholine. These compounds have been shown to possess promising histone deacetylase inhibition activities via in vitro fluorometric assay and molecular docking studies.
Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde
Tanyeli, Cihangir; ERDEM, Mine; ÇAKIR, Esen; KESKİN, Eda (Elsevier BV, 2007-09-27)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. ...
Asymmetric synthesis of norbornene based 1,4-Aminoalcohol derivatives and applications in asymmetric diethylzinc reactions
Erdem, Mine; Tanyeli, Cihangir; Department of Chemistry (2007)
The asymmetric synthesis of chiral norbornene based 1,4-aminoalcohols and their applications in asymmetric diethylzinc addition reactions was perfomed starting from meso-anhydride 50. The desymmetrization of this meso-anhydride 50 was done by the usage of quinine or quinidine cinchona alkaloids with very high enantiomeric excess values (up to 98% ee) and chemical yields. The Quinidine-mediated desymmetrization of meso-anhydride 50 with methanol gave (2R,3S)-(+)-cis-monoester 51. The amination of this result...
Citation Formats
C. Bolm, C. Tanyeli, A. Grenz, and C. Dinter, “ROMP-polymers, in asymmetric catalysis: The role of the polymer backbone,” ADVANCED SYNTHESIS & CATALYSIS, pp. 649–656, 2002, Accessed: 00, 2020. [Online]. Available: