Pregled bibliografske jedinice broj: 1207679
Chiral Brønsted acid-catalyzed synthesis of isoindolinone derivatives containing 3-alkyl tetrasubstituted stereogenic center
Chiral Brønsted acid-catalyzed synthesis of isoindolinone derivatives containing 3-alkyl tetrasubstituted stereogenic center // XLVI "A. Corbella" International Summer School on Organic Synthesis, ISOS 2022 : Book of Abstracts
Gargnano, Italija, 2022. str. 86-86 (predavanje, međunarodna recenzija, sažetak, znanstveni)
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Naslov
Chiral Brønsted acid-catalyzed synthesis of
isoindolinone derivatives containing 3-alkyl
tetrasubstituted stereogenic center
Autori
Matišić, Mateja ; Gredičak, Matija
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni
Izvornik
XLVI "A. Corbella" International Summer School on Organic Synthesis, ISOS 2022 : Book of Abstracts
/ - , 2022, 86-86
Skup
XLVI "A. Corbella" International Summer School on Organic Synthesis, ISOS 2022
Mjesto i datum
Gargnano, Italija, 12.07.2022. - 16.07.2022
Vrsta sudjelovanja
Predavanje
Vrsta recenzije
Međunarodna recenzija
Ključne riječi
Organocatalysis ; Isoindolinone derivatives ; 3-alkyl tetrasubstituted stereogenic center ; Chiral Brønsted acid
Sažetak
Isoindolinone derivatives with a 3-alkyl tetrasubstituted stereogenic center are structure cores present in a broad array of natural and biologically active molecules. Strategies for the construction of such stereocenters in isoindolinones rely on employment of non-aromatic carbon nucleophiles – enones, N-acetyl enamides and difluoroenoxysilanes – in stereoselective Mannich-type reactions. The main drawbacks of these methodologies are inherent inability of employed nucleophiles to generate vicinal stereogenic centers in products, including the control of its diastereo- and enantioselectivity. Herein, we report a chiral phosphoric acid- catalyzed stereoselective addition of ketones to N-acyl ketimines, generated in situ from 3-hydroxy isoindolinones, for the construction of 3-alkyl- aryl stereocenter in isoindolinones. In the reaction mediated by (R)-TRIP, a broad range of ketones and ketimines afforded isoindolinone derivatives comprising a tetrasubstituted stereocenter in high yields and enantioselectivities (Scheme 1). The developed methodology has been successfully extended to the construction of compounds with vicinal stereogenic centers in high diastereomeric and enantiomeric ratios. In addition to the scale-up reaction, selected products were successfully submited to various postmodification transformations. The mechanism of stereochemical induction is also discussed.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
POVEZANOST RADA
Ustanove:
Institut "Ruđer Bošković", Zagreb
