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Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanesстатья
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: 17 ноября 2021 г.
- Авторы: Vartanova Anna E., Plodukhin Andrey Yu, Ratmanova Nina K., Andreev Ivan A., Anisimov Mikhail N., Gudimchuk Nikita B., Rybakov Victor B., Levina Irina I., Ivanova Olga A., Trushkov Igor V., Alabugin Igor V.
- Журнал: Journal of the American Chemical Society
- Год издания: 2021
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Номер статьи: jacs.1c07088
- DOI: 10.1021/jacs.1c07088
- Аннотация: The importance of intramolecular constraints in cyclic transition-state geometries is especially pronounced in n-endo-tet cyclizations, where the usual backside approach of a nucleophile to the breaking bond is impossible for the rings containing less than eight atoms. Herein, we expand the limits of endo-tet cyclizations and show that donor–acceptor cyclopropanes can provide a seven-membered ring via a genuine 6-endo-tet process. Substrates containing a N-alkyl-N-arylcarbamoyl moiety as an acceptor group undergo Lewis acid-induced cyclization to form tetrahydrobenz[b]azepin-2-ones in high yields. The reaction proceeds with the inversion of the configuration at the electrophilic carbon. In this process, a formally six-membered transition state yields a seven-membered ring as the pre-existing cycle is merged into the forming ring. The stereochemistry of the products can be controlled by the reaction time and by the nature of Lewis acid, opening access to both diastereomers by tuning of the reaction conditions.
- Добавил в систему: Плодухин Андрей Юрьевич
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