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A fully diastereoselective oxidation of a mesoionic dipole with triplet molecular oxygen

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Abstract

Oxidations with molecular oxygen are ubiquitous processes in biological systems where cofactor-dependent enzymes activate either oxygen or hydrogen peroxide to induce multichannel pathways. In stark contrast, such slow atmospheric oxidations are seldom harnessed in chemical synthesis and analysis. The present study unveils an unusual aerobic oxidation of a mesoionic dipole leading easily to a more functionalized skeleton. Although the synthetic scope has not been explored, two key considerations emerge from this transformation, as it proceeds with complete diastereoselection and could be successfully extrapolated to structurally related mesoionic chirons without racemization. How this oxidation actually occurs proved to be puzzling from the onset and only high-level computation reveals a cascade transformation, whose results reconcile theory and experiment. Hopefully, the mechanistic insights should help us to understand better the autoxidative reactions of organic molecules.

Graphical abstract: A fully diastereoselective oxidation of a mesoionic dipole with triplet molecular oxygen

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Supplementary files

Article information


Submitted
10 Jul 2020
Accepted
31 Jul 2020
First published
31 Jul 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

A fully diastereoselective oxidation of a mesoionic dipole with triplet molecular oxygen

J. García de la Concepción, M. Ávalos, J. L. Jiménez, P. Cintas and M. E. Light, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01428A

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