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GaCl3-Mediated "Inverted" Formal [3+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Allylic Systemsстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 22 февраля 2019 г.
- Авторы: Zotova Maria A., Novikov Roman A., Shulishov Evgeny V., Tomilov Yury V.
- Журнал: Journal of Organic Chemistry
- Том: 83
- Номер: 15
- Год издания: 2018
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 8193
- Последняя страница: 8207
- DOI: 10.1021/acs.joc.8b00959
- Аннотация: A new process of "inverted" formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes (DACs) to allylic systems to give polyfunctionalized cyclopentanes has been developed. Unlike the classical version of formal [3 + 2]-cycloaddition, a DAC acts in this process as a two-carbon synthon (1,2-zwitterionic reactivity type), while an alkene acts as a three carbon synthon. Tetramethylethylene, allylbenzenes, homoallylbenzene, terminal and internal aliphatic alkenes, and methylenecyclobutane were successfully used as alkenes. Furthermore, in order to suppress annulation at the aromatic ring in 2-arylcyclopropane-1,1-dicarboxylates and enhance the selectivity of the reaction with the allylic system of alkenes, we suggested a new approach for managing the reactivity of DACs involving substitution at both ortho positions of the aromatic ring. Multinuclear NMR spectroscopy was used to study the structure of the 1,2-zwitterionic gallium complexes generated and their properties and to examine the mechanisms of the occurring reactions.
- Добавил в систему: Белая (Зотова) Мария Алексеевна