prikaz prve stranice dokumenta Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses
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master's thesis
Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. urn:nbn:hr:149:871764
Petković, Silvija
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Petković, S. (2015). Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:871764

Petković, Silvija. "Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:871764

Petković, Silvija. "Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:871764

Petković, S. (2015). 'Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:871764

Petković S. Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2015 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:871764

S. Petković, "Preparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2015. Available at: https://urn.nsk.hr/urn:nbn:hr:149:871764

Metadata
TitlePreparation of chiral [2]paracyclo(5,8)quinolinophane - based cinchonoid analogue organocatalysts for stereoselective syntheses
Title (croatian)Priprava kiralnih derivata cinhonidina na [2]paraciklo(5,8)kinolinofanu kao organokatalizatora u stereoselektivnim sintezama
AuthorSilvija Petković
MentorSvjetlana Krištafor (mentor)
Committee memberSvjetlana Krištafor (predsjednik povjerenstva)
Committee memberLidija Furač (član povjerenstva)
Committee memberNataša Perin (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2015-07-13, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Applied Chemistry
Abstract
The aim of this thesis was to synthesize chiral cinchonoid analogues, [2](5,8)quinolinophane and quinoline organocatalysts that could be used in stereoselective syntheses. The presence of the quinoline system makes the molecule of quinolinophane a great "building block" for the synthesis of chiral cinchona analogues as potential organocatalysts. In other words, it would be sufficient to introduce into the molecule a tertiary amino group and a chiral carbon bounded to a hydroxyl group to obtain a molecule that has all the elements of chirality as the natural cinchonoids. The only difference lies in the fact that a central chirality associated with quinuclidine ring of cinchonoids is replaced by the planar chirality associated with the system "quinolinophane". In addition, the quinolinophane constitutes a chiral "building block" of extreme versatility. In fact, through simple transformations, it is possible to obtain different structural combinations in which the determined elements for the asymmetric induction (the tertiary amino group, the hydroxylated chiral carbon and the planar chirality system) can be differently assembled. With that in mind, the scope was to determine contribution of planar and central chirality of (R)-[2]paracyclo[2](5,8)quinolinophane derivatives exhibiting both type of chirality to the asymmetric induction (Figure 1). For sake of comparison envisaged was to prepare also some chiral (S)- and (R)-trifluoromethylsulfoxyamide derived from 4-bromoquinoline.
Abstract (croatian)
Cilj ovog rada bio je sintetizirati kiralne analoge cinhonoidina, [2]paraciklo(5,8)kinolinofane i kinolinske organokatalizatore koji bi se mogli koristiti u stereoselektivnim sintezama. Zbog prisutnosti kinolinskog sustava molekula kinolinofana je izvrstan building block za sintezu kiralnih cinchona analoga kao potencijalnih organokatalizatora. Drugim riječima, dovoljno je uvesti u molekulu tercijarnu amino skupinu i kiralni ugljik vezan na hidroksilnu skupinu, čime se dobije molekula koja ima sve elemente kiralnosti kao prirodni cinchonoidi. Jedina razlika je u tome što je centralna kiralnost povezana s kinuklidinskim prstenom cinchonoida zamjenjena planarnom kiralnošću kinolinofanskog sustava. Nadalje, kinolinofan predstavlja kiralni building block izuzetne raznovrsnosti. U stvari, jednostavnim transformacijama moguće je dobiti različite strukturne kombinacije u kojoj su utvrđeni elementi za asimetričnu indukciju (tercijarna amino skupina, hidroksilirani kiralni ugljik, planarni kiralni sustav). Imajući to na umu, opseg je utvrditi doprinos planarne i središnje kiralnosti (R)-[2]paraciklo[2](5,8)kinolinofanskih derivata koji pokazuju oba tipa kiralnosti u asimetričnoj indukciji (Slika 1). Radi usporedbe pripremljeni su i kiralni (S)- i (R)-trifluorometilsulfoksiamidi izvedeni iz 4-bromkinolina.
Keywords
Keywords (croatian)
Languageenglish
URN:NBNurn:nbn:hr:149:871764
Study programmeTitle: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
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Created on2016-12-09 12:18:55