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Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F16%3A00093871" target="_blank" >RIV/00216224:14740/16:00093871 - isvavai.cz</a>

  • Result on the web

    <a href="http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600471/abstract;jsessionid=7A316B02D70DA68F1146CBD0E83FD9BA.f04t03?systemMessage=Pay+per+view+article+purchase%28PPV%29+on+Wiley+Online+Library+will+be+unavailable+on+Saturday+11th+March+from+05%3A00-14%" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600471/abstract;jsessionid=7A316B02D70DA68F1146CBD0E83FD9BA.f04t03?systemMessage=Pay+per+view+article+purchase%28PPV%29+on+Wiley+Online+Library+will+be+unavailable+on+Saturday+11th+March+from+05%3A00-14%</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/ejoc.201600471" target="_blank" >10.1002/ejoc.201600471</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions

  • Original language description

    The synthesis of new N-carbamoyl-substituted isoxazolidine-4,5-diols and their 4,5-anhydro analogues, isoxazolidinyl epoxides, is described. The 4,5-unsubstituted 2,3-dihydroisoxazole starting materials reacted directly with potassium osmate/4-methylmorpholine N-oxide and 3,3-dimethyldioxirane, respectively. All addition reactions proceeded with excellent anti selectivity with respect to the substituent at C-3. The obtained isoxazolidinyl epoxides as well as benzoylated isoxazolidine-4,5-diols were subjected to nucleophilic substitution reactions with various nucleophiles. 4-Hydroxyisoxazolidines with chlorine, methoxy, and azide substituents bound to C-5 were prepared in moderate to good yields. In terms of chemical stability, the discussed isoxazolidinyl epoxides can be isolated and stored for a long time.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/LM2011020" target="_blank" >LM2011020: CEITEC ? open access</a><br>

  • Continuities

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

Others

  • Publication year

    2016

  • 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

    23

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    10

  • Pages from-to

    3993-4002

  • UT code for WoS article

    000382962700012

  • EID of the result in the Scopus database