Počet záznamů: 1

N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic beta-amino ester enolates

  1. 1.
    SYSNO ASEP0332983
    Druh ASEPJ - Článek v odborném periodiku
    Zařazení RIVJ - Článek v odborném periodiku
    NázevN,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic beta-amino ester enolates
    Tvůrce(i)Jahn, Ullrich (UOCHB-X) - Kafka, František (UOCHB-X) - Pohl, Radek (UOCHB-X) - Jones, P.G. (GB)
    Celkový počet autorů4
    Rozsah stran10917 - 10929
    Zdroj.dok.Tetrahedron. - : Elsevier - ISSN 0040-4020
    Poč.str.13 s.
    Jazyk dok.eng - angličtina
    Země vyd.GB - Velká Británie
    Klíč. slovaelectron transfer ; pyrrolidines ; oxidation
    Vědní obor RIVCC - Organická chemie
    CEZAV0Z40550506 - UOCHB-X (2005-2011)
    UTISI000272918300021
    DOI10.1016/j.tet.2009.10.034
    AnotaceOxidative 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.
    PracovištěÚstav organické chemie a biochemie
    KontaktJana Procházková, janap@uochb.cas.cz, Tel.: 220 183 418 ; Michaela Záluská, zaluska@uochb.cas.cz, Tel.: 232 002 579
    Rok sběru2010