Počet záznamů: 1
Mechanistic Exploration of Umpolung Guided Stetter-Aldol Reaction and Its Dependence on the Choice of Imine
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SYSNO ASEP 0567234 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Mechanistic Exploration of Umpolung Guided Stetter-Aldol Reaction and Its Dependence on the Choice of Imine Tvůrce(i) Barman, D. (IN)
Lo, Rabindranath (UOCHB-X) ORCID, RID
Maiti, D. K. (IN)
Manna, D. (IN)
Ghosh, T. (IN)Číslo článku e202204558 Zdroj.dok. ChemistrySelect. - : Wiley - ISSN 2365-6549
Roč. 8, č. 1 (2023)Poč.str. 7 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova umpolung ; Breslow intermediate ; free energy profile ; density functional theory ; isoquinoline Obor OECD Physical chemistry Způsob publikování Omezený přístup Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000913403600018 EID SCOPUS 85146319176 DOI 10.1002/slct.202204558 Anotace NHC-catalyzed Stetter-aldol reaction for the synthesis of hydroxyindanone takes place via umpolung reactions of phthalaldehyde followed by intramolecular aldol reaction when N-tert-butoxycarbonyl (Boc) imine is used and this leads to the formation of [4+1] annulation product. However, this mechanism doesn't follow similar sequence in case of N-tosyl-alpha,beta-unsaturated ketimine and [4+2]-annulation product is found as the sole product for the latter case through formation of aza-“Berslow intermediate“. In this study we have used state of the art computational techniques to find out the possible reason for the difference in product and the detailed mechanistic pathway for the above two reactions. Thus, we explain the mechanism for obtaining the selective annulation product ([4+1] vs [4+2]) that can help chemists to design and synthesize a new series of compounds. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2024 Elektronická adresa https://doi.org/10.1002/slct.202204558
Počet záznamů: 1