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Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffoldстатья
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 10 апреля 2024 г.
- Авторы: Ikonnikova Viktoria A., Cheibas Cristina, Gayraud Oscar, Bosnidou Alexandra E., Casaretto Nicolas, Frison Gilles, Nay Bastien
- Журнал: Beilstein Journal of Organic Chemistry
- Том: 20
- Год издания: 2024
- Издательство: Beilstein-Institut
- Местоположение издательства: Germany
- Первая страница: 162
- Последняя страница: 169
- DOI: 10.3762/bjoc.20.15
- Аннотация: The Hock cleavage, which is compatible with tandem processes, was applied to the synthesis of 1-aryltetralines through a one-pot transformation from readily available benzyl(prenyl)malonate substrates. After the photooxygenation of the prenyl moiety, the resulting hydroperoxide was directly engaged in a Hock cleavage by adding a Lewis acid. The presence of an aromatic nucleophile in the reaction mixture and that of a benzyl moiety on the substrate resulted in tandem Friedel–Crafts reactions to form the 1-aryltetraline products. These compounds share a close analogy to the cyclolignan natural products. Experimental observations and a DFT study support the involvement of an aldehyde intermediate during the Friedel–Crafts reactions, rather than an oxocarbenium.
- Добавил в систему: Иконникова Виктория Алексеевна