Direct regio- and stereoselective mono- and polyoxyfunctionalization of estrone derivatives at C(sp3)-H bonds Full article
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Journal of Catalysis
ISSN: 0021-9517 , E-ISSN: 1090-2694 |
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| Output data | Year: 2022, Volume: 415, Pages: 12-18 Pages count : 7 DOI: 10.1016/j.jcat.2022.09.020 | ||||||||
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Abstract:
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.
Cite:
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
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
Dates:
| Submitted: | Aug 1, 2022 |
| Accepted: | Sep 19, 2022 |
| Published online: | Sep 30, 2022 |
| Published print: | Oct 5, 2022 |
Identifiers:
| Web of science: | WOS:000875426600002 |
| Scopus: | 2-s2.0-85139301479 |
| Elibrary: | 50357026 |
| OpenAlex: | W4298149872 |