Direct Regio- and Stereoselective Mono- and Polyoxyfunctionalization of Estrone Derivatives at C(sp3)-H Bonds | Sciact - CRIS-система Института катализа

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

Ключевые слова

Biomimetic chemistry; C[sbnd]H activation; Late-stage functionalization; Natural products; Steroids

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

Информация о финансировании (3)

1	Российский научный фонд	22-73-00080
2	Министерство науки и высшего образования Российской Федерации (с 15 мая 2018)	FWUZ-2021-0001 (121031700321-3)
3	Министерство науки и высшего образования Российской Федерации (с 15 мая 2018)	0238-2021-0005 (АААА-А21-121011490018-2)

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.

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 CAPlusCA OpenAlex

Поступила в редакцию:	1 авг. 2022 г.
Принята к публикации:	19 сент. 2022 г.
Опубликована online:	30 сент. 2022 г.
Опубликована в печати:	1 нояб. 2022 г.

Web of science:	WOS:000875426600002
Scopus:	2-s2.0-85139301479
РИНЦ:	50357026
Chemical Abstracts:	2022:2574602
Chemical Abstracts (print):	182:48302
OpenAlex:	W4298149872

БД	Цитирований
Scopus	12
Web of science	12
РИНЦ	11
OpenAlex	12