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Mechanistic Exploration of Umpolung Guided Stetter-Aldol Reaction and Its Dependence on the Choice of Imine
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SYSNO ASEP 0567234 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Mechanistic Exploration of Umpolung Guided Stetter-Aldol Reaction and Its Dependence on the Choice of Imine Author(s) Barman, D. (IN)
Lo, Rabindranath (UOCHB-X) ORCID, RID
Maiti, D. K. (IN)
Manna, D. (IN)
Ghosh, T. (IN)Article number e202204558 Source Title ChemistrySelect. - : Wiley - ISSN 2365-6549
Roč. 8, č. 1 (2023)Number of pages 7 s. Language eng - English Country DE - Germany Keywords umpolung ; Breslow intermediate ; free energy profile ; density functional theory ; isoquinoline OECD category Physical chemistry Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000913403600018 EID SCOPUS 85146319176 DOI 10.1002/slct.202204558 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2024 Electronic address https://doi.org/10.1002/slct.202204558
Number of the records: 1