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N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions
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SYSNO ASEP 0463910 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions Author(s) Kafka, František (UOCHB-X)
Pohl, Radek (UOCHB-X) RID, ORCID
Císařová, I. (CZ)
Mackman, R. (US)
Bahador, G. (US)
Jahn, Ullrich (UOCHB-X) ORCIDSource Title European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2016, č. 22 (2016), s. 3862-3871Number of pages 10 s. Language eng - English Country DE - Germany Keywords tandem reactions ; nitrogen heterocycles ; Michael addition ; radical reactions ; cyclization ; enolates Subject RIV CC - Organic Chemistry R&D Projects GA13-40188S GA ČR - Czech Science Foundation (CSF) Institutional support UOCHB-X - RVO:61388963 UT WOS 000382768400027 EID SCOPUS 84978394400 DOI 10.1002/ejoc.201600621 Annotation Enantioselective syntheses of densely functionalized pyrrolidines deriving their chirality from (R)-1-(phenyl) ethylamine are reported. Allylic amines and beta-substituted-alpha, beta-unsaturated esters are used as the building blocks in this one-pot reaction. Single electron transfer (SET) oxidation served to merge the reactivities of anionic enolate and radical intermediates. Ferrocenium hexafluorophosphate, which is easy to prepare, store and handle, was applied as SET oxidant and persistent free radical TEMPO served as the oxygenating agent introducing a protected hydroxy function, which proved to be beneficial for further derivatization. Exclusive 2,3-trans and up to 6: 1 3,4-cis/trans diastereoselectivities were achieved in the targeted tetrasubstituted pyrrolidines. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2017
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