Počet záznamů: 1
N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions
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SYSNO ASEP 0463910 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions Tvůrce(i) Kafka, František (UOCHB-X)
Pohl, Radek (UOCHB-X) RID, ORCID
Císařová, I. (CZ)
Mackman, R. (US)
Bahador, G. (US)
Jahn, Ullrich (UOCHB-X) ORCIDZdroj.dok. European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2016, č. 22 (2016), s. 3862-3871Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova tandem reactions ; nitrogen heterocycles ; Michael addition ; radical reactions ; cyclization ; enolates Vědní obor RIV CC - Organická chemie CEP GA13-40188S GA ČR - Grantová agentura ČR Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000382768400027 EID SCOPUS 84978394400 DOI 10.1002/ejoc.201600621 Anotace 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. 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 2017
Počet záznamů: 1