Straightforward Synthetic Approach to Aminoalcohols with 9-oxabicyclo[3.3.1]nonane or Cyclooctane Core via Nucleophilic Ring-Opening of Spirocyclic Bis(oxiranes)

Ryzhikova, O.V.; Savchenkova, D.V.; Kositov, S.V.; Grishin, Y.K.; Maloshitskaya, O.A.; Sedenkova, K.N.; Averina, E.B.

Авторы: Ryzhikova Olga V., Savchenkova Daiana V., Kositov Sergey V., Grishin Yuri K., Maloshitskaya Olga A., Sedenkova Kseniya N., Averina Elena B.
Журнал: Molecules
Том: 31
Номер: 2
Год издания: 2026
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Номер статьи: 252
DOI: 10.3390/molecules31020252
Аннотация: Nucleophilic ring-opening of bis(oxiranes), containing several reactive centers, can be used to elaborate straightforward atom-economy and stereoselective approaches to polyfunctionalized compounds. In the present work, ring-opening of cis- and trans-diastereomers of a spirocyclic bis(oxirane), containing a cyclooctane core (namely, 1,8-dioxadispiro[2.3.2.3]dodecane), upon treatment with various amines, was studied. Trans-isomer afforded aminoalcohols with 9-oxabicyclo[3.3.1]nonane moiety, formed via domino-process, including opening of an oxirane ring followed by intramolecular cyclization.Ring-opening of cis-isomer gave aminosubstituted cis-cyclooctane-1,5-diols, derived from independent reaction of two oxirane moieties. Activation of oxirane rings by the addition of LiClO4, acting as a Lewis acid, allowed the involvement of a number of primary and secondary aliphatic amines as well as aniline derivatives in the reaction. Scope and limitations of the reaction were studied and a series of aminoalcohols with a 9-oxabicyclo[3.3.1]nonane core and symmetric diaminodiols with a cyclooctane core were obtained.
Добавил в систему: Седенкова Ксения Николаевна

	ИСТИНА	Войти в систему Регистрация
	Интеллектуальная Система Тематического Исследования НАукометрических данных
	Главная Поиск Статистика О проекте Помощь

ИСТИНА

Интеллектуальная Система Тематического Исследования НАукометрических данных

Straightforward Synthetic Approach to Aminoalcohols with 9-oxabicyclo[3.3.1]nonane or Cyclooctane Core via Nucleophilic Ring-Opening of Spirocyclic Bis(oxiranes)статья Исследовательская статья

Прикрепленные файлы