Luka Ciber (Author), Sebastijan Ričko (Author), Jure Gregorc (Author), Franc Požgan (Author), Jurij Svete (Author), Helena Brodnik Žugelj (Author), Bogdan Štefane (Author), Uroš Grošelj (Author)

Abstract

Arylidene-Δ2-pyrrolin-4-ones undergo organocatalyzed annulation with malononitrile, furnishing dihydropyrano[3,2-b]pyrroles (18 examples, 0–77% ee in dichloromethane, 11–44% ee in methanol). The products could be enantiomerically enriched by trituration (11 examples, 95–99% ee). Enantioselectivity was dependent on the nature of the substrate and the conformation of the catalyst, which in turn was solvent-controlled. The reaction mechanism, which included two pseudo-enantiomeric organocatalyst conformations, was investigated by experimental and quantum chemical methods. The reaction mechanism consists of Michael addition reaction step followed by 6-exo-dig annulation, which was found to be the rate determining step. Additionally, it was identified that the preferred reaction pathway follows the model originally proposed by Pápai et al.

Keywords

organokataliza;asimetrična sinteza;enantioselektivnost;učinki topil;piroloni;psevdo-enantiomerne konformacije katalizatorja;organocatalysis;asymmetric synthesis;enantioselectivity;solvent effects;pyrrolone;pseudo-enantiomeric catalyst conformations;

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.74:544.47
COBISS: 97278211 Link will open in a new window
ISSN: 1615-4150
Views: 204
Downloads: 15
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Other data

Secondary language: Slovenian
Secondary keywords: organokataliza;asimetrična sinteza;enantioselektivnost;učinki topil;piroloni;psevdo-enantiomerne konformacije katalizatorja;
Type (COBISS): Article
Embargo end date (OpenAIRE): 2023-01-14
Pages: str. 980-993
Volume: ǂVol. ǂ364
Issue: ǂiss. ǂ5
Chronology: 1 Mar. 2022
DOI: 10.1002/adsc.202101369
ID: 14536735