Asimetrični prijenos vodika na 3-aril-3-ketoestere - primjena u sintezi kiralnih molekula sa svojstvima tekućih kristala

master's thesis

• Title (english): Asymmetric transfer hydrogenation of 3-aryl-3-ketoesters - Application in the synthesis of chiral molecules with liquid crystal properties
• Author: Matija Hromin
• Mentor: Irena Dokli (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Sanda Rončević (član povjerenstva)
• Committee member: Željka Soldin (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2021-09-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog istraživačkog rada pripremljeni su 3-aril-3-ketoesteri, etil 3-(6-(benziloksi)naft2-il)-3-oksopropanoat i etil 3-(4'-(benziloksi)-[1,1'-bifenil]-4-il)-3-oksopropanoat, koji su
iskorišteni za ispitivanje stereoselektivne redukcije keto skupine asimetričnim prijenosom
vodika uz rutenijeve(II) katalizatore i ligand N-((1S,2S)-2-amino-1,2-difeniletil)piperidin-1-
sulfonamid. Pripravljeni etil 3-(6-(benziloksi)naft-2-il)-3-hidroksipropanoat, odnosno (S)-etil
3-(6-(benziloksi)naft-2-il)-3-hidroksipropanoat iskorišteni su za sintezu racemičnog i kiralnog
6-(3-(heksiloksi)-1-hidroksi-3-oksopropil)naftalen-2-il 4-(heksiloksi)benzoata kojima su
ispitana mezogena svojstva.

Abstract (english)

In the scope of this work two 3-aryl-3-ketoesters were prepared, ethyl 3-(6-
(benzyloxy)naphthalen-2-yl)-3-oxopropanoate and ethyl 3-(4'-(benzyloxy)-[1,1'-biphenyl]-4-
yl)-3-oxopropanoate, which were used to examine stereoselective reduction of the keto group
by asymmetric transfer hydrogenation performed with ruthenium (II) catalysts and ligand N-
((1S,2S)-2-amino-1,2-diphenylethyl)piperidine-1-sulfonamide. Prepared compounds, ethyl 3-
(6-(benzyloxy)naphthalen-2-yl)-3-hydroxypropanoate and (S)-ethyl 3-(6-
(benzyloxy)naphthalen-2-yl)-3-hydroxypropanoate were used for synthesis of racemic and
chiral 6-(3-(hexyloxy)-1-hydroxy-3-oxopropyl)naphthalen-2-yl 4-(hexyloxy)benzoate
in order to observe their mesogenic properties.

• Keywords: 3-aril-3-ketoesteri; asimetrični prijenos vodika; rutenij; tekući kristali
• Keywords (english): 3-aryl-3-ketoesters; asymmetric transfer hydrogenation; liquid crystals; rhutenium
• Language: croatian
• URN:NBN: urn:nbn:hr:217:588305
• Project: Number: IP-2019-04-7978; Title: Strukturna kiralnost vs molekulska kiralnost; Title: Structural Chirality vs Molecular Chirality; Acronym: SMChiral; Leader: Andreja Lesac; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-10-15 11:28:05