Počet záznamů: 1
N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic beta-amino ester enolates
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SYSNO ASEP 0332983 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic beta-amino ester enolates Tvůrce(i) Jahn, Ullrich (UOCHB-X) ORCID
Kafka, František (UOCHB-X)
Pohl, Radek (UOCHB-X) RID, ORCID
Jones, P.G. (GB)Celkový počet autorů 4 Zdroj.dok. Tetrahedron. - : Elsevier - ISSN 0040-4020
Roč. 65, č. 52 (2009), s. 10917-10929Poč.str. 13 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova electron transfer ; pyrrolidines ; oxidation Vědní obor RIV CC - Organická chemie CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000272918300021 DOI 10.1016/j.tet.2009.10.034 Anotace Oxidative radical cyclizations starting from easily accessible N-allylic beta-alanine esters are reported. Deprotonation generates the corresponding enolates, which are transformed efficiently into alpha-ester radicals by single electron transfer mediated by ferrocenium hexafluorophosphate. The stereochemistry of the radical 5-exo cyclization can be switched by the configuration of the enolate precursor. First examples of asymmetric oxidative radical cyclizations using N-(1-phenylethyl)-substituted beta-amino esters are reported. Only two of the four possible diastereomers are formed from the (E)-enolate with high cis-selectivity. From (Z)-enolates, an additional diastereomer is formed, which is likely to be formed only under chelation control. 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 2010
Počet záznamů: 1