Synthesis and reactions of alpha-keto-beta-hydroxyphosphonates

Download

index.pdf

Date

2007

Author

Barış, Şehriban

Metadata

Show full item record

Item Usage Stats

298
views

107
downloads

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 with organocatalysts for the enantioselective formation of desired products.

Subject Keywords

Chemistry, Organic

URI

http://etd.lib.metu.edu.tr/upload/3/12608215/index.pdf
https://hdl.handle.net/11511/16681

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Development of acyl anion precursors and their applications Reis, Ömer; Demir, Ayhan Sıtkı; Department of Chemistry (2005) This thesis presents the development of new acyl anion precursors and their applications. The main concern of this thesis was to make use of acyl anion precursors in catalytic bond forming reactions. Toward this aim, previously known cyanide ion catalyzed cleavage of benzils was investigated in scope and efficiency in unsymmetrical benzoin condensation. Although benzils were proved to be useful entities as acyl anion precursors in benzoin condensation, they suffer some major drawbacks. Therefore acylphospho...
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...
Self condensation reaction of alpha-ketophosphonates Göllü, Mehmet; Demir, Ayhan Sıtkı; Department of Chemistry (2007) This thesis presents synthesis of tertiary α-hydroxy phosphonate derivatives. α-Ketophosphonates is known that they are both acyl anion precursors and electrophiles. In this work, α-ketophosphonates were used as both acyl anion precursors and electrophiles in the presence of catalytic amount of KCN. α-Ketophosphonates underwent benzoin-type condensation reaction.
Synthesis of 3-[(4-Nitrophenyl)thio]-Substituted 4-Methylene-1-pyrrolines from N-Propargylic beta-Enaminones Korkmaz, Esra; Zora, Metin (American Chemical Society (ACS), 2020-04-03) A facile and efficient method for the synthesis of 3-[(4-nitrophenyl)thio]-substituted 4-methylene-1-pyrrolines is described. When treated with 4-nitrobenzenesulfenyl chloride in refluxing acetonitrile, N-propargylic beta-enaminones produced alpha-sulfenylated N-propargylic beta-enaminones, which, in the presence of sodium hydride or cesium carbonate, underwent nucleophilic cyclization to afford 4-methylene-3-[(4-nitrophenyl)thio]-1-pyrrolines in good to high yields. It was shown for the first time that on ...
Synthesis of beta-chloro-alpha-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates Polat-Cakir, Sidika; BEKSULTANOVA, Nurzhan; Doğan, Özdemir (Informa UK Limited, 2018-12-02) A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.

Citation Formats

Ş. Barış, “Synthesis and reactions of alpha-keto-beta-hydroxyphosphonates,” M.S. - Master of Science, Middle East Technical University, 2007.