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master's thesis
Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. urn:nbn:hr:149:357209
Bašić, Ines
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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Bašić, I. (2018). Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:357209

Bašić, Ines. "Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:357209

Bašić, Ines. "Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:357209

Bašić, I. (2018). 'Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 02 January 2025, https://urn.nsk.hr/urn:nbn:hr:149:357209

Bašić I. Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2018 [cited 2025 January 02] Available at: https://urn.nsk.hr/urn:nbn:hr:149:357209

I. Bašić, "Asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:149:357209

Metadata
TitleAsimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama
Title (english)Chiral phoshoric acid-catalyzed asymmetric synthesis of N,O-acetals comprising quatenary stereogenic center
AuthorInes Bašić
MentorIrena Škorić (mentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberDanijela Ašperger (član povjerenstva)
Committee memberMatija Gredičak (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2018-10-31, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U ovom radu prikazana je asimetrična priprava N,O-acetala s kvaternim stereogenim centrom katalizirana kiralnim fosfornim kiselinama. Istraživanja su pokazala da kiralni N,Oacetali predstavljaju važne funkcionalne skupine u prirodnim spojevim s antiproliferativnim djelovanjem te stabilizirajućim djelovanjem na mikrotubule. Isoindolinonski derivati N,O-acetala poznati su inhibitori MDM2-p53 protein-protein interakcija. Kondenzacijom ftalimida sa fenilmagnezij bromidom, 2-tienil litijem i (3,5-diklorofenil)magnezij bromidom pripremljeni su spojevi 1, 2 i 3. U reakciji spoja 1 i benzilnog alkohola odnosno cikloheksanola, kataliziranoj fenil fosfinskom kiselinom, pripravljeni su spojevi 5 i 6. U reakcijama benzilnog alkohola sa različitim 3-supstituiranim-3-hidroksiisoindolinonima pripremljeni su spojevi 7-12. Strukture priređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom, te spektrometrijom masa. Stupanj enantioselektivnosti određen je na kiralnim kolonama na HPLC-u.
Abstract (english)
Within this work, asymmetric preparation of N,O-acetals with quaternary stereogenic center catalyzed by chiral phosporic acid is presented. According to previous research, chiral N,O-acetals represent important functional groups in natural compounds with antiproliferative activity and with stabilizing effect on microtubules. Isoindolinone N,O-acetal derivatives are well known inhibitors of MDM2-p53 protein-protein interactions. The condensation of phtalimide with phenylmagnesium bromide, 2-thienyl lithium and (3,5-dichlorophenil)magnesium bromide yielded compunds 1, 2 and 3. In a reaction catalysed by phenyl phospinic acid, compund 1 reacted with benzyl alcohol or cyclohexanol to afford compunds 5 and 6. In reactions of benzyl alcohol with different 3-substituted-3-hydroxyisoindolinones compunds 7-12 were prepared. Structures of prepared compounds were confirmed by 1H i 13C NMR spectroscopy, as well as mass spectrometry. Enantiomeric ratio was determined by chiral HPLC.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:357209
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 on2022-02-15 13:49:14