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Transition Metal-Catalyzed Direct Stereoselective Oxygenations of C(sp3)–H Groups Обзор

Журнал ACS Catalysis
ISSN: 2155-5435
Вых. Данные Год: 2023, Том: 13, Номер: 16, Страницы: 10770-10795 Страниц : 6 DOI: 10.1021/acscatal.3c02282
Ключевые слова asymmetric catalysis biomimetic catalysis C−H activation oxidation mechanism selectivity
Авторы Bryliakov Konstantin P. 1
Организации
1 Zelinsky Institute of Organic Chemistry RAS, Leninsky Pr. 47, Moscow 119991, Russia

Реферат: Designing catalytic approaches to deliberate and selective C–H activation was listed by Bergman among the “Holy Grails” of synthetic chemistry in 1995, and continues to be a hot topic up to now, mostly in the context of late-stage functionalization of complex molecular structures ( Acc. Chem. Res. 1995, 28, 154−162, DOI: 10.1021/ar00051a009). This contribution surveys the asymmetric oxygenations of aliphatic C–H groups of organic molecules that have been reported to date, including enantio- and diastereoselective hydroxylations at prochiral C–H groups and oxidative desymmetrizations (through either ketonization or hydroxylation), via direct creation of new C–O bonds with the aid of synthetic transition metal based catalysts. Catalytic stereoselective C(sp3)–H oxygenations of complex structures of relevance for developing synthetic approaches for late-stage functionalization of bioactive molecules (such as, mostly, steroids and terpenoids) for drug discovery and development are considered. Synthetic aspects of the oxidative transformations as above are the major focus of the review. The mechanistic bases of the above processes are discussed briefly, in connection to the factors that govern the oxidation regio-, chemo-, and stereoselectivity.
Библиографическая ссылка: Bryliakov K.P.
Transition Metal-Catalyzed Direct Stereoselective Oxygenations of C(sp3)–H Groups
ACS Catalysis. 2023. V.13. N16. P.10770-10795. DOI: 10.1021/acscatal.3c02282 WOS Scopus РИНЦ CAPlusCA OpenAlex
Даты:
Поступила в редакцию: 19 мая 2023 г.
Принята к публикации: 13 июл. 2023 г.
Опубликована online: 3 авг. 2023 г.
Опубликована в печати: 18 авг. 2023 г.
Идентификаторы БД:
Web of science: WOS:001141856200001
Scopus: 2-s2.0-85168510928
РИНЦ: 62738584
Chemical Abstracts: 2023:1594457
Chemical Abstracts (print): 183:329723
OpenAlex: W4385501652
Цитирование в БД:
БД Цитирований
OpenAlex 21
Web of science 22
Scopus 22
Альметрики: