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Title: Synthesis of novel multi-functionalized pyrrolidines by [3 + 2] dipolar cycloaddition of azomethine ylides and vinyl ketones
Authors: Pešić, Marko
Bugarinović, Jovana
Minić, Aleksandra
Ilić Komatina D.
Pejović, Anka
Šmit, Biljana
Stevanović, Dragana
Damljanović, Ivan
Issue Date: 2019
Abstract: © 2019, Springer-Verlag GmbH Austria, part of Springer Nature. Abstract: An efficient and easy synthetic route to substituted pyrrolidine derivatives has been established through [3 + 2] dipolar cycloaddition of vinyl ketones and azomethine ylides. The reactions proceed smoothly, under mild conditions, affording moderate to high isolated yields (up to 88%) of the products, within a short reaction time (15–45 min), providing a series of novel potentially bioactive compounds. Mechanistic considerations revealed that this cycloaddition exclusively proceeds following endo-pathway which enables access to the cis-derivatives. The products that contain acetyl group at C4 easily undergo isomerization, as it was confirmed by monitoring of the reaction kinetics and DFT calculations. Graphical abstract: [Figure not available: see fulltext.].
Type: article
DOI: 10.1007/s00706-018-2340-6
ISSN: 0026-9247
SCOPUS: 2-s2.0-85062553815
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac

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