Selectivity of Oxidizing Agents toward Axial and Equatorial Hydroxyl Groups

0559495 - ÚOCHB 2023 RIV US eng J - Článek v odborném periodiku
Kašpar, Miroslav - Kudová, Eva
Selectivity of Oxidizing Agents toward Axial and Equatorial Hydroxyl Groups.
Journal of Organic Chemistry. Roč. 87, č. 14 (2022), s. 9157-9170. ISSN 0022-3263. E-ISSN 1520-6904
Grant CEP: GA MZd(CZ) EF16_025/0007444; GA TA ČR(CZ) TN01000013
Institucionální podpora: RVO:61388963
Klíčová slova: secondary alcohols * dimethyl-sulfoxide * oxidation
Obor OECD: Organic chemistry
Impakt faktor: 3.6, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1021/acs.joc.2c00877

A total of 16 oxidizing reagents were screened to compare their oxidation selectivities for axial and equatorial hydroxyl moieties using steroidal methyl chenodeoxycholate, methyl deoxycholate, and 4-tert-butylcyclohexanol (cis/trans 1:1 mixture). These compounds were selected for their stable chair conformations. The results of our study demonstrated that, for the oxidation of a scaffold bearing both axial and equatorial hydroxyl groups, nitroxide-radical-based reagents should be the first choice if oxidation of the equatorial hydroxyl group is needed and Stevens or Dess-Martin reagents should be the first choice for the preferential oxidation of the axial hydroxyl group.
Trvalý link: https://hdl.handle.net/11104/0332776