Issue 42, 2014

α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with triplet oxygen

Abstract

Trimethylaluminum and molecular oxygen are used in tandem to interrupt the Nazarov cyclization. α-Hydroxycyclopentanones are produced in moderate to good yield as a mixture of epimers. This sequence is the first example of combined nucleophilic/electrophilic trapping of the Nazarov oxyallyl intermediate.

Graphical abstract: α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with triplet oxygen

Supplementary files

Article information

Article type
Communication
Submitted
28 Mar 2014
Accepted
11 Apr 2014
First published
14 Apr 2014

Chem. Commun., 2014,50, 5558-5560

α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with triplet oxygen

Y. Kwon, O. Scadeng, R. McDonald and F. G. West, Chem. Commun., 2014, 50, 5558 DOI: 10.1039/C4CC02330G

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