Regio- and stereoselective [2+2] photocycloaddition in Ba2+ templated supramolecular dimers of styryl-derivatized aza-heterocycles

The regio- and stereoselective [2+2] photocycloaddition of 15-crown-5-containing styrylheterocycles resulting in formation of only one cyclobutane isomer out of eleven possible is described. It was shown that the cycloaddition takes place solely in the case of the supramolecular preorganization of the reactive molecules provided by both π–π stacking interaction of the heterocyclic fragments and sandwich-type coordination of the crown ether residues by the barium cation. The results point out the importance of the supramolecular approach for the synthesis of cyclobutane derivatives with desired structure and conformation. © 2016 Elsevier Ltd

Авторы
Berdnikova D.V. 1, 2 , Aliyeu T.M.1 , Delbaere S.3 , Fedorov Y.V.1 , Jonusauskas G.4 , Novikov V.V.1 , Pavlov A.A.1 , Peregudov A.S.1 , Shepel' N.E.1 , Zubkov F.I. 2 , Fedorova О.A.1
Журнал
Издательство
Elsevier Ltd
Язык
Английский
Страницы
397-402
Статус
Опубликовано
Том
139
Год
2017
Организации
  • 1 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str. 28, Moscow, 119991, Russian Federation
  • 2 RUDN University, Mikluho-Maklaya Str. 6, Moscow, 117198, Russian Federation
  • 3 University of Lille, UDSL, CNRS UMR 8516, Lille, BP83, France
  • 4 Laboratoire Ondes et Matière d'Aquitaine, Université Bordeaux 1, 351 Cours de la Libération, Talence, 33405, France
Ключевые слова
Crown ethers; Dimers; Stereoselectivity; Aza-heterocycles; Cyclobutanes; Pi-stacking; Preorganization; Sandwich types; Stereo-selective; Templated; [2+2] photocycloaddition; Supramolecular chemistry
Дата создания
19.10.2018
Дата изменения
12.08.2021
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/5569/
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