Transition Metal-Catalyzed Direct Stereoselective Oxygenations of C(sp3)–H Groups Review
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ACS Catalysis
ISSN: 2155-5435 |
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| Output data | Year: 2023, Volume: 13, Number: 16, Pages: 10770-10795 Pages count : 6 DOI: 10.1021/acscatal.3c02282 | ||
| Tags | asymmetric catalysis biomimetic catalysis C−H activation oxidation mechanism selectivity | ||
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Abstract:
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.
Cite:
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 ANCAN OpenAlex
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 ANCAN OpenAlex
Dates:
| Submitted: | May 19, 2023 |
| Accepted: | Jul 13, 2023 |
| Published online: | Aug 3, 2023 |
| Published print: | Aug 18, 2023 |
Identifiers:
| Web of science: | WOS:001141856200001 |
| Scopus: | 2-s2.0-85168510928 |
| Elibrary: | 62738584 |
| Chemical Abstracts: | 2023:1594457 |
| Chemical Abstracts (print): | 183:329723 |
| OpenAlex: | W4385501652 |