Issue 42, 2014
From the journal:

Chemical Communications

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

Yonghoon Kwon,a   Owen Scadeng,a   Robert McDonalda  and  F. G. West*a  

* Corresponding authors

a Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada
E-mail: frederick.west@ualberta.ca
Fax: +1 780 492 8231
Tel: +1 780 492 8187

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

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Article information

DOI
https://doi.org/10.1039/C4CC02330G
Article type
Communication
Submitted
28 Mar 2014
Accepted
11 Apr 2014
First published
14 Apr 2014

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

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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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