Selectivity of Oxidizing Agents toward Axial and Equatorial Hydroxyl Groups

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-07, Vol.87 (14), p.9157-9170
Main Authors: Kaspar, Miroslav, Kudova, Eva
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00877