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Asymmetric Epoxidation vs syn-Hydroxy-Acyloxylation of Olefins in the Presence of Sterically Demanding Nonheme Manganese Complexes. / Sherstyuk, Varvara A.; Ottenbacher, Roman V.; Talsi, Evgenii P. и др.

в: ACS Catalysis, Том 14, № 1, 05.01.2024, стр. 498-507.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

Harvard

Sherstyuk, VA, Ottenbacher, RV, Talsi, EP & Bryliakov, KP 2024, 'Asymmetric Epoxidation vs syn-Hydroxy-Acyloxylation of Olefins in the Presence of Sterically Demanding Nonheme Manganese Complexes', ACS Catalysis, Том. 14, № 1, стр. 498-507. https://doi.org/10.1021/acscatal.3c04832

APA

Vancouver

Sherstyuk VA, Ottenbacher RV, Talsi EP, Bryliakov KP. Asymmetric Epoxidation vs syn-Hydroxy-Acyloxylation of Olefins in the Presence of Sterically Demanding Nonheme Manganese Complexes. ACS Catalysis. 2024 янв. 5;14(1):498-507. doi: 10.1021/acscatal.3c04832

Author

Sherstyuk, Varvara A. ; Ottenbacher, Roman V. ; Talsi, Evgenii P. и др. / Asymmetric Epoxidation vs syn-Hydroxy-Acyloxylation of Olefins in the Presence of Sterically Demanding Nonheme Manganese Complexes. в: ACS Catalysis. 2024 ; Том 14, № 1. стр. 498-507.

BibTeX

@article{d3835060db6e4a56a9c2275ef9938952,
title = "Asymmetric Epoxidation vs syn-Hydroxy-Acyloxylation of Olefins in the Presence of Sterically Demanding Nonheme Manganese Complexes",
abstract = "Herewith, we present another facet of the versatile catalytic reactivity of bulky bis-amino-bis-pyridylmethyl Mn complexes: besides highly enantioselective (up to 99% ee) epoxidation, benzhydryl-substituted Mn catalysts have been found to convert olefinic substrates into the products of syn-addition to the C═C bond, hydroxy-carboxylates, that can prevail under certain conditions. The mechanism of syn-hydroxy-acyloxylation is discussed, with the data obtained providing evidence in favor of the so far lacking direct enantioselective OH and OC(O)R transfer from the high-valent Mn active species to the olefinic C═C group. Such a mechanism is conceptually reminiscent of Rieske dioxygenases that catalyze enantioselective 1,2-dihydroxylation of C═C bonds, simultaneously incorporating two cis-ligands from the reactive metal center into the resulting diol in a syn-selective fashion.",
keywords = "asymmetric catalysis, biomimetic chemistry, epoxidation, hydrogen peroxide, manganese, syn-addition",
author = "Sherstyuk, {Varvara A.} and Ottenbacher, {Roman V.} and Talsi, {Evgenii P.} and Bryliakov, {Konstantin P.}",
note = "The authors thank the Ministry of Science and Higher Education of the Russian Federation for the financial support of this work and acknowledge the access to the facilities of the shared research center “National center of investigation of catalysts”, kindly provided by the Boreskov Institute of Catalysis.",
year = "2024",
month = jan,
day = "5",
doi = "10.1021/acscatal.3c04832",
language = "English",
volume = "14",
pages = "498--507",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "1",

}

RIS

TY - JOUR

T1 - Asymmetric Epoxidation vs syn-Hydroxy-Acyloxylation of Olefins in the Presence of Sterically Demanding Nonheme Manganese Complexes

AU - Sherstyuk, Varvara A.

AU - Ottenbacher, Roman V.

AU - Talsi, Evgenii P.

AU - Bryliakov, Konstantin P.

N1 - The authors thank the Ministry of Science and Higher Education of the Russian Federation for the financial support of this work and acknowledge the access to the facilities of the shared research center “National center of investigation of catalysts”, kindly provided by the Boreskov Institute of Catalysis.

PY - 2024/1/5

Y1 - 2024/1/5

N2 - Herewith, we present another facet of the versatile catalytic reactivity of bulky bis-amino-bis-pyridylmethyl Mn complexes: besides highly enantioselective (up to 99% ee) epoxidation, benzhydryl-substituted Mn catalysts have been found to convert olefinic substrates into the products of syn-addition to the C═C bond, hydroxy-carboxylates, that can prevail under certain conditions. The mechanism of syn-hydroxy-acyloxylation is discussed, with the data obtained providing evidence in favor of the so far lacking direct enantioselective OH and OC(O)R transfer from the high-valent Mn active species to the olefinic C═C group. Such a mechanism is conceptually reminiscent of Rieske dioxygenases that catalyze enantioselective 1,2-dihydroxylation of C═C bonds, simultaneously incorporating two cis-ligands from the reactive metal center into the resulting diol in a syn-selective fashion.

AB - Herewith, we present another facet of the versatile catalytic reactivity of bulky bis-amino-bis-pyridylmethyl Mn complexes: besides highly enantioselective (up to 99% ee) epoxidation, benzhydryl-substituted Mn catalysts have been found to convert olefinic substrates into the products of syn-addition to the C═C bond, hydroxy-carboxylates, that can prevail under certain conditions. The mechanism of syn-hydroxy-acyloxylation is discussed, with the data obtained providing evidence in favor of the so far lacking direct enantioselective OH and OC(O)R transfer from the high-valent Mn active species to the olefinic C═C group. Such a mechanism is conceptually reminiscent of Rieske dioxygenases that catalyze enantioselective 1,2-dihydroxylation of C═C bonds, simultaneously incorporating two cis-ligands from the reactive metal center into the resulting diol in a syn-selective fashion.

KW - asymmetric catalysis

KW - biomimetic chemistry

KW - epoxidation

KW - hydrogen peroxide

KW - manganese

KW - syn-addition

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85181805299&origin=inward&txGid=d7ee08bd83606a1f84c59f1f2f282b8e

UR - https://www.mendeley.com/catalogue/b72aba5f-6548-3962-bcc1-f17e62b7176d/

U2 - 10.1021/acscatal.3c04832

DO - 10.1021/acscatal.3c04832

M3 - Article

VL - 14

SP - 498

EP - 507

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 1

ER -

ID: 61294334