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Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F19%3A73596934" target="_blank" >RIV/61989592:15110/19:73596934 - isvavai.cz</a>

  • Alternative codes found

    RIV/61989592:15310/19:73596934

  • Result on the web

    <a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.8b02465" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.8b02465</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.joc.8b02465" target="_blank" >10.1021/acs.joc.8b02465</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture

  • Original language description

    This report describes a configuration-dependent [6+8+5] fused ring formation via a tandem cyclic N-acyliminium-nucleophilic addition reaction. Cyclization of the acyclic precursor prepared on the solid phase using L-Ser and racemic mixture of Fmoc-trans-2-aminocyclohexane carboxylic acid predominantly yielded the cyclic diastereomer with the (1R,2R)-2-aminocyclohexane moiety rather than the tricyclic diastereomer from the (1S,2S)-enantiomer. In contrast, the model compound prepared with D-Ser predominantly cyclized with the (1S,2S)-2-aminocyclohexane carboxylic acid substrate. The outcome of the cyclization was not influenced by the type of resin, the spacer or the N-substituent. The analogous synthesis of the [6+7+5] fused ring system yielded an inseparable diastereomers in a 1:0.6 ratio.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2019

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    JOURNAL OF ORGANIC CHEMISTRY

  • ISSN

    0022-3263

  • e-ISSN

  • Volume of the periodical

    84

  • Issue of the periodical within the volume

    2

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    9

  • Pages from-to

    636-644

  • UT code for WoS article

    000456632800016

  • EID of the result in the Scopus database

    2-s2.0-85059645550