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Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones Научная публикация

Журнал Molecules
ISSN: 1420-3049
Вых. Данные Год: 2021, Том: 26, Номер: 24, Номер статьи : 7539, Страниц : 19 DOI: 10.3390/molecules26247539
Ключевые слова Bispidines; Catalysis; Chalcones; Chiral ligands; Dialkylzincs addition; Ethylation; Monoterpenoids; Natural compounds; Nickel complexes
Авторы Suslov Evgeniy V. 1 , Ponomarev Konstantin Y. 1 , Patrusheva Oxana S. 1 , Kuranov Sergey O. 1 , Okhina Alina A. 1,2 , Rogachev Artem D. 1,2 , Munkuev Aldar A. 1 , Ottenbacher Roman V. 3 , Dalinger Alexander I. 4 , Kalinin Mikhail A. 4 , Vatsadze Sergey Z. 4 , Volcho Konstantin P. 1 , Salakhutdinov Nariman F. 1
Организации
1 Department of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, Russia
2 Faculty of Natural Sciences, Novosibirsk State University, Pirogov Str., 2, 630090 Novosibirsk, Russia
3 Boreskov Institute of Catalysis SB RAS, Lavrent’ev Av., 5, 630090 Novosibirsk, Russia
4 Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, MSU, 1-3, 119991 Moscow, Russia

Информация о финансировании (1)

1 Российский научный фонд 19-73-20090 (АААА-А19-119050790033-6)

Реферат: A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed, in which the peaks of the enantiomers of all synthesized chiral products were separated, which made it possible to determine the enantiomeric excess of the resulting mixture. It was demonstrated that bispidine-monoterpenoid conjugates can be used as the ligands for diethylzinc addition to chalcone C=C double bond but not as inducers of chirality. Besides products of ethylation, formation of products of formal hydrogenation of the chalcone C=C double bond was observed in all cases. Note, that this formation of hydrogenation products in significant amounts in the presence of such catalytic systems was found for the first time. A tentative scheme explaining the formation of all products was proposed. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
Библиографическая ссылка: Suslov E.V. , Ponomarev K.Y. , Patrusheva O.S. , Kuranov S.O. , Okhina A.A. , Rogachev A.D. , Munkuev A.A. , Ottenbacher R.V. , Dalinger A.I. , Kalinin M.A. , Vatsadze S.Z. , Volcho K.P. , Salakhutdinov N.F.
Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones
Molecules. 2021. V.26. N24. 7539 :1-19. DOI: 10.3390/molecules26247539 WOS Scopus РИНЦ CAPlus PMID OpenAlex
Даты:
Поступила в редакцию: 27 нояб. 2021 г.
Опубликована в печати: 2 дек. 2021 г.
Принята к публикации: 10 дек. 2021 г.
Опубликована online: 13 дек. 2021 г.
Идентификаторы БД:
Web of science: WOS:000745034900001
Scopus: 2-s2.0-85121206812
РИНЦ: 47542556
Chemical Abstracts: 2022:91642
PMID (PubMed): 34946622
OpenAlex: W4200463881
Цитирование в БД:
БД Цитирований
Scopus 8
РИНЦ 13
Web of science 8
OpenAlex 7
Альметрики: