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Article Dans Une Revue Journal of Organic Chemistry Année : 2024

Utilization of $^{13}$C NMR Carbon Shifts for the Attribution of Diastereomers in Methyl-Substituted Cyclohexanes

Résumé

In this report, we address the challenge of assigning diastereomers for methyl cyclohexanes, particularly those with quaternary centers, which remains nontrivial despite modern NMR techniques. By utilizing a HSQC NMR experiment to identify methyl-carbons coupled with a simple conformational analysis, we identified an effective and quite general method for assigning stereochemistry, even in cases where diastereomeric mixtures are inseparable.
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hal-04614347 , version 1 (24-06-2024)

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Daniel S. Müller, Paul Charki, Marie Cordier, Urs Gellrich. Utilization of $^{13}$C NMR Carbon Shifts for the Attribution of Diastereomers in Methyl-Substituted Cyclohexanes. Journal of Organic Chemistry, 2024, 89 (12), pp.8668-8675. ⟨10.1021/acs.joc.4c00602⟩. ⟨hal-04614347⟩
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