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Direct regio- and stereoselective mono- and polyoxyfunctionalization of estrone derivatives at C(sp3)-H bonds Научная публикация

Журнал Journal of Catalysis
ISSN: 0021-9517 , E-ISSN: 1090-2694
Вых. Данные Год: 2022, Том: 415, Страницы: 12-18 Страниц : 7 DOI: 10.1016/j.jcat.2022.09.020
Авторы Ottenbacher Roman V. 1 , Samsonenko Denis G. 2 , Nefedov Andrey A. 3,4 , Bryliakov Konstantin P. 1,4
Организации
1 Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk 630090, Russia
2 Nikolaev Insitute of Inorganic Chemistry, Lavrentieva 3, Novosibirsk 630090, Russia
3 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Lavrentieva 9, Novosibirsk 630090, Russia
4 Novosibirsk State University, Pirogova 1, Novosibirsk 630090, Russia

Реферат: Late-stage catalytic selective oxidative C-H functionalization at B and C rings of estrone 3-acetate, 17α- and 17β-estradiol 3-acetates with H2O2 in the presence of bioinspired nonheme Mn complexes with N4-donor ligands has been developed. Depending on the ligand architecture and absolute chirality, products of α-hydroxylation or ketonization at C6, or α-hydroxylation at C9, or 9,11-desaturation/C12α-hydroxylation can be obtained in synthetically useful yields; the resulting monooxygenated derivatives can be involved in further selective oxidative transformations to yield polyoxygenated metabolites. The aromatic A ring remains intact under the conditions, and ketonization of the hydroxo groups at C17 is effectively prevented by using hexafluoroisopropanol as strong hydrogen bond donor reaction solvent.
Библиографическая ссылка: Ottenbacher R.V. , Samsonenko D.G. , Nefedov A.A. , Bryliakov K.P.
Direct regio- and stereoselective mono- and polyoxyfunctionalization of estrone derivatives at C(sp3)-H bonds
Journal of Catalysis. 2022. V.415. P.12-18. DOI: 10.1016/j.jcat.2022.09.020 WOS Scopus РИНЦ OpenAlex
Даты:
Поступила в редакцию: 1 авг. 2022 г.
Принята к публикации: 19 сент. 2022 г.
Опубликована online: 30 сент. 2022 г.
Опубликована в печати: 5 окт. 2022 г.
Идентификаторы БД:
Web of science: WOS:000875426600002
Scopus: 2-s2.0-85139301479
РИНЦ: 50357026
OpenAlex: W4298149872
Цитирование в БД:
БД Цитирований
Web of science 11
Scopus 12
РИНЦ 11
OpenAlex 12
Альметрики: