Naslov
Organocatalytic asymmetric transformations of 3-substituted 3-hydroxyisoindolinones

Autori
Gredičak, Matija

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog : knjiga sažetaka = 25th Croatian Meeting of Chemist and Chemical Engineers with international participation. 3rd symposium “Vladimir Prelog” : Book of Abstracts / Šantić, Ana ; Đaković, Marijana - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI) ; Hrvatsko kemijsko drustvo, 2017, 67-67

ISBN
978-953-552327-7

Skup
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem ; 3. simpozij Vladimir Prelog = 25th Croatian Meeting of Chemist and Chemical Engineers with international participation. 3rd symposium “Vladimir Prelog”

Mjesto i datum
Poreč, Hrvatska, 19.04.2017. - 22.04.2017

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Nije recenziran

Ključne riječi
asymmetric catalysis ; isoindolinones ; thiol addition ; aza-Friedel-Crafts reaction

Sažetak
3-Substituted isoindolinones and their derivatives are common structural motifs in a variety of compounds with biological activities. For example, they have been established as precursors to anti– ischemic stroke agents, as well as antimicrobial and antitumor agents. Their activity as MDM2–p53 protein– protein, HIV–1 integrase, and protein-tyrosine phosphatase inhibitors is also well known. In addition, registered and commercially available anxiolytic, anticonvulsant and antihypertensive drugs also contain 3-substituted isoindolinone cores. Hence, it is of great importance to develop facile and effective methods for their asymmetric synthesis. In our group, we are interested in developing asymmetric organocatalytic transformations generating cores of natural compounds. As a part of an ongoing project, we have developed chiral Brønsted-acid catalyzed asymmetric additions of nucleophiles to ketimines, that are generated in situ from 3-substituted 3- hydroxyisoindolinones. The asymmetric addition of thiols provided chiral N(acyl), S-acetals in high isolated yields and excellent enantioselectivities, and the application of the developed protocol was demonstrated in the synthesis of a known HIV-1 reverse transcriptase inhibitor. In a similar fashion, asymmetric Friedel-Crafts reaction resulted in high yields and enantioselectivities of products comprising triarylsubstituted stereocentres, an important motif in the cores of natural compounds.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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