Synthesis of heteroaryl substituted dihydrofuran and dihydropyran derivatives by green chemistry approach

Download

index.pdf

Date

2009

Author

Demirci, Sema

Metadata

Show full item record

Item Usage Stats

345
views

156
downloads

The thesis subject is mainly involved in Green Chemistry approach. Thiophene, furan and pyridine carboxaldehydes were chosen as starting compounds and vinylation and allylation with Grignard reaction afforded the corresponding racemic heteroaryl substituted allylic and homoallylic alcohols. Subsequent resolution with enzymes (PS-Amano II, Lipozym and Novazym 435) gave enantiomerically enriched alcohols with the e.e. values varied between 65 and 99%. The absolute configurations of all substrates are known. As a result of O-allylation with the common procedure formed the feasible carbon backbone for the ring closing metathesis reaction. All ring closing metathesis reactions were performed by Grubbs’ catalyst with just 5% catalyst loading. The absolute configurations of dihydrofuran and dihydropyran derivatives are known, since the chiral center configurations of all substrates are preserved throughout all the applied processes.

Subject Keywords

Chemistry., Chemistry, Organic

URI

http://etd.lib.metu.edu.tr/upload/2/12610966/index.pdf
https://hdl.handle.net/11511/19056

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis of linkers and mediators for electrochemical reactor design and enantiopure synthon preparation Akbaşoğlu, Naime; Demir, Ayhan Sıtkı; Department of Chemistry (2009) The thesis subject is mainly involved in Green Chemistry approach. Thiophene, furan and pyridine carboxaldehydes were chosen as starting compounds and vinylation and allylation with Grignard reaction afforded the corresponding racemic heteroaryl substituted allylic and homoallylic alcohols. Subsequent resolution with enzymes (PS-Amano II, Lipozym and Novazym 435) gave enantiomerically enriched alcohols with the e.e. values varied between 65 and 99%. The absolute configurations of all substrates are known. A...
Oxidation of organic sulfides by N-halamine compounds Akdağ, Akın; Worley, S. D. (Informa UK Limited, 2007-07-01) N-halamine chemistry has been an important research topic in these laboratories for over two decades, offering many exciting opportunities both from practical and pedagogical points of view. One of these opportunities is in the use of polymer- and silica gel-bound N-halamines as selective oxidizing agents for organosulfur compounds. In this study, they have been employed to selectively oxidize organic sulfides including dimethyl sulfide and chloroethyl ethyl sulfide, the chemical mustard stimulant. The latt...
Synthesis and enzymatic resolution of various cyclopentenoid and cyclohexenoid type compounds İyigün, Çiğdem; Tanyeli, Cihangir; Department of Chemistry (2005) The aim of this thesis is to synthesize enantiomerically enriched cyclopentenoid and cyclohexenoid type of compounds with quaternary carbon stereocenters that are the simplest precursors of the complex natural products. The first part of the study involves the preparation of ?'-acetoxy ?'-substituted ?,β-unsaturated cyclic ketones. Methylation, ethylation, benzylation and allylation of cyclohexenone and cyclopentenone derivatives are performed. Then, these compounds are regioselectively oxidized at the ?'-p...
Synthesis and reactions of alpha-keto-beta-hydroxyphosphonates Barış, Şehriban; Demir, Ayhan Sıtkı; Department of Chemistry (2007) This thesis presents synthesis and different reactions of alpha-keto-beta-hydroxyphosphonates. Toward this aim, the hydroxyl functionality of alpha-hydroxycarboxylic acids were protected with alkyl or acyl groups and then formation of acid chloride followed by the reaction with trialkylphosphite furnished protected alpha-keto-beta-hydroxyphosponates. Nucleophilic addition reactions were applied to these compounds to obtain quaternary alcohols with phosphonate functionality. The addition reactions were tried...
Synthesis of various camphor-based chiral pyridine derivatives Işık, Murat; Tanyeli, Cihangir; Department of Chemistry (2005) Chiral aromatic nitrogen heterocycles are finding many applications in asymmetric organic synthesis, particularly as ligands in the preparation of chiral metal complexes. Since camphor-based chiral auxiliaries are known to be especially effective, a number of pyridines fused to the camphor skeleton have been reported. It is well known that nicotinic acid and its derivatives exhibiting qualitatively the biological activity of nicotinamide, which acts as an electron acceptor in many biological redox reactions...

Citation Formats

S. Demirci, “Synthesis of heteroaryl substituted dihydrofuran and dihydropyran derivatives by green chemistry approach,” M.S. - Master of Science, Middle East Technical University, 2009.