New Potential Sugar-Ferrocenyl Imine Catalysts Synthesis and Their Characterizations via Spectroscopic Methods

Year 2024, Volume: 29 Issue: 2, 483 - 493, 31.08.2024

Cansu Özkara , Özer Işılar , Adnan Bulut

https://doi.org/10.53433/yyufbed.1471479

Abstract

Sugars are natural stereoisomers and can be defined as polyhydroxycarbonyl compounds. The derivatization of them gives us new purifiable sugar diastereomers. Enantioselective reactions are aimed to occur on a single surface of the molecule, that is, "re-face" or "si-face". The size (steric effect) and enantiopurity of sugar can enable us to achieve this goal. For this purpose, the sugar-derived chiral Schiff bases were synthesized and characterized by spectroscopic methods (1H NMR, 13C NMR, and IR). In the synthetic part, amino sugars were obtained in three steps. These are, tosylating the free hydroxyl, converting it into azide derivatives, and reduction to amino sugars, respectively. In the last step of the synthetic section, ferrocene-2-carboxaldehyde and amino sugars were converted into novel ferrocene-sugar-imine derivatives by condensation reaction.

Keywords

Ferrocene, Schiff Base, Sugar

Yeni Potansiyel Şeker-Ferrosenil İmin Katalizörler Sentezi ve Spektroskopik Yöntemlerle Karakterizasyonu

Abstract

Şekerler doğal stereoizomerlerdir ve polihidroksikarbonil bileşikleri olarak tanımlanabilirler. Yeni türevlerine geçiş, bize yeni saflaştırılabilen şeker türevi diastereomerler vermektedir. Enantiyoselektif tepkimelerin molekülün tek yüzeyinden, yani “re-face” ya da “si-face” yönünden olması hedeflenir. Şekerin büyüklüğü (sterik engeli) ve kiral yapısı, asimetrik tepkimelerde enantiyoseçiciliği sağlayabilir. Bu amaç doğrultusunda şeker türevi kiral Schiff bazları sentezlenmiştir ve spektroskopik yöntemler (1H NMR, 13C NMR ve IR) ile karakterize edilmiştir. Sentetik bölümde ilk olarak amino şekerler üç basamakta elde edilmiştir. Bunlar sırası ile serbest hidroksili tosilleme, azür türevine çevirme ve amino şeker sentezleridir. Sentetik bölümün son basamağında ferrosen-2-karboksaldehit ile sentezlenen amino şekerler kondenzasyon tepkimesi ile literatürde bilinmeyen ferrosen-şeker türevi kiral imin türevlerine çevrilmiştir.

Keywords

Ferrosen, Schiff bazı, Şeker

Thanks

Bu çalışma TÜBİTAK 114Z688 no’lu proje ile desteklenmiştir. TÜBİTAK’a verdiği destekten dolayı teşekkür ederiz.

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