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Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10383302" target="_blank" >RIV/00216208:11310/18:10383302 - isvavai.cz</a>

  • Alternative codes found

    RIV/61388963:_____/18:00495570

  • Result on the web

    <a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=5RTW0N49r-" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=5RTW0N49r-</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/ejoc.201800485" target="_blank" >10.1002/ejoc.201800485</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Chiral Unsymmetrically Substituted Bipyridine N,N-Dioxides as Catalysts for the Allylation of Aldehydes

  • Original language description

    A series of unsymmetrically substituted diastereoisomeric (R-a,R) and (S-a,R) bipyridine N,N-dioxides was synthesized by using oxidative coupling of the corresponding metallated tetrahydroisoquinoline N-oxides in the presence of iodine. The N,N-dioxides contained substituted aryl groups with electron-donating or electron-accepting groups in the near vicinity of the N,N-dioxide moiety. Their catalytic activity was tested in a series of reactions of allyltrichlorosilane with various substituted benzaldehydes, thiophenecarbaldehyde, and cinnamaldehyde. The reactions proceeded with high enantioselectivities (up to 98% ee) with catalyst loadings as low as 0.5 mol-%. Furthermore, allylation reactions of (E)-3-iodomethacrylaldehyde were also carried out to give chiral (E)-1-iodo-2-methylpenta-1,4-dien-3-ol, a convenient building block for the synthesis of natural products. The allylations proceeded with high enantioselectivities (up to ca. 99% ee) with a catalyst loading of 2.5 mol-%.

  • 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

    <a href="/en/project/GA17-07707S" target="_blank" >GA17-07707S: Development of New Syntheses of Azaheterocycles</a><br>

  • Continuities

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

Others

  • Publication year

    2018

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    European Journal of Organic Chemistry

  • ISSN

    1434-193X

  • e-ISSN

  • Volume of the periodical

    neuveden

  • Issue of the periodical within the volume

    37

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    8

  • Pages from-to

    5109-5116

  • UT code for WoS article

    000446662900005

  • EID of the result in the Scopus database

    2-s2.0-85050502907